In short
Fashion designer Jamie Haller discusses her career pivots and how she built her eponymous brand across shoes, later apparel, and home renovation. Backgrounds: She started in corporate retail design in the 2000s at Wet Seal (production then design), then denim at Guess, then sportswear/outerwear at BB. She later worked at smaller wholesale companies (Ever Clothing, NSF) with more creative freedom, and also became a yoga teacher after health issues she links to corporate life.
Key claims
COVID pushed her to launch shoes despite having “no experience,” using intuition and “seketto” construction for her signature loafer.
Notable examples
She renovated historic homes for years (duplexes, flips, craftsman houses) and credits that aesthetic learning to her design. Her penny loafer grew slowly from one shoe in 2020 to major press (Wirecutter’s Best Loafer) and led to apparel (Ready-to-Wear launched fall 2024), plus a Montecito brick-and-mortar store she designed herself.
Guests
Jamie Haller; host Hilary Kerr (co-founder of Who What Where).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOJamie's Journey to Fashion Design
0:46 to 1:56
Jamie shares her unexpected path to becoming a fashion designer.
“While Jamie's career did start in fashion, her first jobs were actually in corporate retail at brands like Wet Seal, Guess, and BB in the 2000s.”
Early Influences and Education
1:57 to 2:45
Jamie discusses her early interests in fashion and her college experience.
“Jamie, thank you so much for doing this.”
Starting at Wet Seal
2:46 to 4:38
Jamie talks about landing her first job at Wet Seal and her early experiences.
“Well, to be honest, it was not on my radar to be a fashion designer.”
Transitioning to Design
4:39 to 7:10
Jamie reflects on moving from production to the design department at Wet Seal.
“These are all things that I do all the time, but it didn't prepare you for what getting a job was like.”
Working at Guess and BB
7:11 to 10:10
Jamie recounts her experiences as a denim designer at Guess and sportswear designer at BB.
“concept of what it meant to work in fashion.”
Lessons from Corporate Retail
10:11 to 12:37
Jamie discusses the lessons learned from her years in corporate retail and the challenges faced.
“People also move in tribes and chunks of people that I was very close with from Wet Seal and R &B, which were the same corporate company, I was really keyed into a lot of the R &B people and they were moving.”
Seeking Change and New Opportunities
12:38 to 13:40
Jamie describes her decision to leave corporate life and explore smaller companies and yoga.
“I was also approaching a time in my life where I was going to make changes.”
Finding Creative Freedom
13:41 to 14:01
Jamie explains the difference in creative freedom she experienced in smaller companies.
“You ended up working for some smaller contemporary wholesale companies, first at Ever Clothing, then at NSF.”
The Freedom of Design at Ever
14:01 to 16:48
Learn about the creative freedom and responsibilities of working in fashion design.
“at a place like BB and working at a place like Ever is one, it felt really cool to work at Ever and I could pick that color pink in two seconds and move on.”
The Shift to Digital Marketing in Fashion
16:49 to 19:18
Discover how digital marketing reshaped fashion production and collection frequency.
“And then depending on the health of the company and cash flow, you know, you start doing these exclusive drops because you don't want there to be a drop in cash flow in April.”
Show all 27 chapters
Staying Inspired Amidst High Production Demands
19:19 to 20:26
Explore creative strategies for maintaining engagement in high-volume design work.
“I would be more inspired by fabric or concepts.”
From Fashion to Home Renovation
20:27 to 22:46
Uncover the journey of transitioning from fashion design to historic home renovation.
“So I want to go back because while all of this is going on and you are having fashion design success, you're also, I believe at the same time dabbling in a totally different space, which is historic home renovation.”
Creative Fulfillment Through Home Projects
22:47 to 24:24
Learn how home renovation provides a fulfilling creative outlet for designers.
“But at this time I had been working on houses for about 10 years.”
Embracing Change During COVID
24:25 to 27:00
Understand the impact of the pandemic on creative ventures and new opportunities.
“Plus, being there so long, I could do it very easily with whatever schedule I wanted.”
Launching a Shoe Line During Uncertainty
27:01 to 28:00
Follow the steps taken to start a shoe line amidst the challenges of COVID.
“and I could interview them and that person introduced me to somebody in Italy, I just kept saying, yes.”
From Hobby to Independence
28:00 to 29:50
Learn how a side project evolved into a significant career shift.
“My first client bought a craftsman in East Hollywood, Larchmont area, and we're not going to move there.”
Launching the Shoe Line
29:50 to 31:40
Discover the journey from a single slipper to a full-fledged shoe brand.
“At what point do you start thinking like, okay, like let's go to production or I have enough ideas to launch something.”
Challenges and Innovations in Shoe Design
31:40 to 33:50
Explore the unique approaches Jamie took in designing her shoes.
“Jamie, that's so many jobs you had at the same time.”
Transitioning to Apparel Design
33:50 to 36:00
Understand the shift from shoes to clothing and the motivations behind it.
“Now it matters if I make money because now I don't have any other income and now I have a staff and production bills, you know?”
Customer-Centric Clothing Philosophy
36:00 to 37:50
Learn how personal experiences influenced the design of clothing for real bodies.
“I just want to play and make and create, and then you have to edit, you know, and I know how to do that too.”
Successful Products and Market Response
37:50 to 40:00
Hear about successful items and how they were received in the market.
“And oh, I mean, the waist tape is like the perfect pant known to mankind.”
Opening a Brick-and-Mortar Store
40:00 to 42:00
Find out what led to the decision of opening a physical store in Montecito.
“and I've just been so grateful to have won over their trust from the beginning.”
The Launch of the Montecito Store
42:00 to 43:36
Jamie discusses her unexpected journey to opening her first store.
“and it's not everything, but the Navy sweatshirt had that moment last spring and it's continues to be very, very strong.”
Expanding Product Lines and Future Plans
43:36 to 45:44
Jamie talks about her new handbag and jewelry lines and future ambitions.
“into handbags, two styles, two colorways, right?”
Learning from Mistakes in Business
45:44 to 47:25
Jamie shares insights on making mistakes and the importance of resilience.
“So on this podcast, we ask the same final three questions every time.”
Advice for Making Career Changes
47:25 to 48:29
Jamie offers practical advice for those considering a career change.
“listen to this podcast are in their first lives and they want to do something different.”
Words of Encouragement to Younger Self
48:29 to 48:58
Jamie reflects on her journey and shares encouraging advice for herself.
“I think I would just say like it's all going to be worth it.”
Transcript
Automatic transcript. May contain errors.0:05Hi, everyone. I'm Hilary Kerr, the co-founder and chief content officer of Who What Where, and this is Second Life, a podcast spotlighting women who have truly inspiring careers. We're talking about their work journeys, what they've learned from the process of setting aside their doubts or fears, and what happens when they embark on their second life. Today on the show, I'm speaking with one of my personal favorite shoe and apparel designers, Jamie Haller. You probably know her from her eponymous brand. The Jamie Haller penny loafers in particular have become an if-you-know-you-know staple amongst the fashion crowd.
0:46While Jamie's career did start in fashion, her first jobs were actually in corporate retail at brands like Wet Seal, Guess, and BB in the 2000s. She eventually left the corporate world to share her vision with smaller brands that gave her more creative control and freedom. When the pandemic hit in 2020, Jamie was itching to try something new, and she found that her taste and instincts lent themselves well to not one but two new areas of design, home renovation and shoes. Although she had no experience in either, she quickly gained interior design clients and became a hit maker in the shoe space.
1:26Last year, Jamie expanded her brand to include apparel, but the clothing she makes is a far cry from her corporate retail days. Today, everything Jamie designs is created from a deeply personal place. And this year, she was able to bring her two worlds closer together than ever with her first brick and mortar store in Montecito, a space she designed herself where people can shop her brand. I love chatting with Jamie and I can't wait for you to hear from her. Now on Second Life, it's Jamie Haller. Jamie, thank you so much for doing this. I feel like it's a long time coming And on a side note, like I continue to be amused by the number of people who will DM me to let me know that they bought your loafers or a pair of pants or whatever, because like you talk about them so much.
2:20Like they feel the need to tell me. I'm like, don't tell me. Tell her. That is really funny.
2:25Jamie Haller:Thank you so much for all of the talking. It's my pleasure. I own so much of your stuff. And I'm really glad that we have a chance to sit down and talk about it. So we can just get right into it. Let's do it. I'm so excited. Okay, good. So we like to start this podcast at the beginning. So Jamie, what did you study in school? And much more importantly, what did you think you were going to be when you grew up? Well, to be honest, it was not on my radar to be a fashion designer. It wasn't what I was expecting because I didn't really know you could work in fashion when I was young. I wasn't exposed to it.
3:02Jamie Haller:I loved fashion. I was a figure skater and I would make all the costumes for my performances and I would design them based on the music or the mood. But it didn't occur to me that I would do it as a job, you know. And so I think when I applied to college, I had the major picked out that I was going to do broadcast journalism because it was like the 90s. And I think that was a really popular major. And you look on a list and you're like, that looks fun. And then life changed and I ended up not going to college right away. And then that fell away. That was never something I thought about again. And I ended up going to community college and then I was a Spanish major and that was like a terrible idea.
3:48Jamie Haller:And instead of going to college, I got booked to be in a movie as a poor extra on the Titanic, which is crazy because I was like 17. So I didn't go to college. I moved to Mexico instead. You know, I got so into speaking Spanish that I came back and I just went to school. And I met somebody though, at a bar, a man that he said he worked in the industry. I was like, what are you talking about? What's the industry for fashion? I was like, you can work in fashion. And as soon as he said, yeah, then I was like, done. I moved to LA like a month later. I changed colleges. I was a fashion design major and I just didn't know you could do it.
4:32Talk to me about your fashion design program in college. What was your experience like?
4:38Jamie Haller:When I look back, I learned things that were very helpful. I learned about patterns. I learned the right way to sew things. I learned how to make garments. I learned how to sketch. I learned how to do illustrator. These are all things that I do all the time, but it didn't prepare you for what getting a job was like. So you still get out of it and you kind of know nothing and you're so naive. But I got a job, so it did something like I did something with it and it all worked out great. So you landed a job at Wet Seal, right? I did. Talk to me about getting that job at Wet Seal. I read that you were initially hired for a production position.
5:19For our folks who might not know, what does that mean exactly?
5:22Jamie Haller:Yeah, well, I was just thrilled to get a job. I was thrilled that it was at Wet Seal because I was 20 and I loved Wet Seal and it was so much fun. I think everybody should start in production. It was so helpful. I learned everything technical about specking garments, making tech packs, communicating with production vendors. Wet Seal didn't produce their own clothes. Like there wasn't an active production team where you're chasing product around LA or wherever. It was all done through outside vendors. But still, you learned so much. I really belonged in design. So after being there for, I don't know, six months, I then moved quickly into the design department.
6:03Jamie Haller:But starting off in production was an amazing way to learn kind of the nuts and bolts of how to make clothes and what that process looks like. For our audience, what exactly is a tech pack? It's kind of like a spec sheet or it's like, if I was going to design a shirt, I would draw a picture of a shirt. I would have to provide the pattern maker or the factory with measurements of like the shoulder and the bust. How long is the collar point and how wide is the placket and how big is the button and what's the spacing between the button? And you blueprint out, you CAD out the entire garment down to like how many stitches per inch do you want the sewing machine to sew, you know?
6:46Jamie Haller:And so you have to kind of get all this information around a garment and communicate it and then cross your fingers that It comes out good. So six months in, you move into the design aspect. What was that like? How did it compare to your idea of what it would be like? And how did it compare to what you had been learning in school? I just don't think I had any idea of anything it would be like. I had no concept of what it meant to work in fashion. Actually, I did do an internship. I'm sure I was like the greenest, weirdest person who knew nothing, but I saw it. You just learn on the job. You learn really fast, you know?
7:25Jamie Haller:And back then it was much different than it is now. Technically it's different. You know, we used to stand in line and fax our faxes out to China every night. And the work culture was very different in 2000 than it is now. People worked really long hours. It was just more intense, but you developed a thick skin and that serves me well, you know. I hear you on that. So talk to me about moving into the design department. What responsibility were you given in those early days? You were assigned to a buyer. And so it was also very categorical. So my category that I designed were bottoms. I would also do some denim.
8:10Jamie Haller:And so you'd be responsible for working with your buyer to get your monthly line plan needs. Like you would stand up and show your designs and then everybody would like tear you apart. Basically, you're always presenting to your buyer. You're always working through the open to buy. I mean, to be honest, it was so amazing because it really gave me a language and the ability to understand merchandising, buying, retail. All of those experiences allowed me to see how a big company works. There's a lot of trend forecasting. There's a lot of going to Europe to shop. You've had to do that to go shop and see something different.
8:48Just the coolest on so many levels. So talk to me about your next couple of moves, because you went on to work as a denim designer at Guess and then as a sportswear and outerwear designer at BB. Were you chasing a specific trajectory? Were you making moves just based on like brands that were interesting to you? How are you figuring out these moves?
9:10Jamie Haller:I don't think I had a strategy in mind. The guest thing kind of fell into my lap. I was unhappy at Wet Seal. A lot of times what happens in corporate companies are there are these big, massive, top-down team changes that occur. And when the new team comes in, it can be very disrupting. For whatever reason, I was like, well, I'm out of here. You know, like I was done. I got offered the job. I really didn't have very much denim experience, but they liked me. And I only lasted a year at Guest. Guest is a pretty tough environment. People get fired quite a lot. I actually got fired from Guest, which is now kind of like a badge of honor, you know?
9:49Jamie Haller:Yep. I know many people who have. Yeah. And when the heads roll, they like roll. It's not like you got fired. It was like 20 people got fired, you know? But I learned so much about denim. I would go to Mexico all the time and be in the wash houses. I learned from an amazing person who knew so much about denim. I would go to China. You know, amazing. I learned so much. People also move in tribes and chunks of people that I was very close with from Wet Seal and R &B, which were the same corporate company, I was really keyed into a lot of the R &B people and they were moving. And so all of a sudden they all showed up at guests And that was weird, but like cool.
10:28Jamie Haller:And then a lot of people had moved on to BB. And so when I got fired, I got a job at BB and I got brought in and I knew people and just kind of how it was back then that people moved around together. What was it like moving to outerwear as a category? Is it technically more difficult? It wasn't technical outerwear. It was like fur coats and suede jackets with fringe and wool coats. And I did sexy suiting is what I call it now, but it was sportswear, but I was a suiting designer and I loved that. I fell in love with suiting. And the cool thing was that we used really amazing fabrics, like all the Italian vendors sold to BB, but you could afford to use really nice fabrics.
11:14Jamie Haller:I work with some people today that I knew from BB Fabric Mills. To that point too, like when you have that level of scale, then suddenly these fabrics can be pretty great. That's what it is too. You know, they're ordering so much. So at this point, you have been in corporate retail for six or seven years. When you look back at that chunk of your career, what are some of the most significant things that that time taught you? And also what made you interested in trying other things? I think corporate is such a double-edged sword. I think that it is amazing. You learn so much. You see a big picture.
11:54Jamie Haller:You could work really closely with people who are so skilled. That's amazing to see somebody working at such a different level when you're young in your career, if they allow you that access. And it is hard to work by consensus in large groups, you could spend two weeks talking about the color pink and 25 people are going to like chime in after a chunk of time, you start to really die on the vine. That's how I felt. Also, as you become more and more experienced or sure of yourself, if it's not aligned with, for me, my truest design sensibilities, you're just doing the job, but I needed to do something that felt more like me and I felt more alignment with.
12:38Jamie Haller:I was also approaching a time in my life where I was going to make changes. I was getting married and I had a child and I needed to not be in that super fast corporate environment where they want you to stay till eight o 'clock every night. I needed a healthier lifestyle. And I think one thing I didn't say is like the coolest part about all of it is all the people that you can form connections with. When I go back and think about it. That's what I think about is like, oh, well, I met my best friend there and that group is still hanging out together. It's like trauma bonds. I was just about to say that.
13:12Jamie Haller:And you look back and you're like, no, it was so fun. But there were days where it wasn't fun too. And to be honest, I was becoming unhealthy. I think I developed like an autoimmune condition. The corporate life structure can be really hard on people mentally, emotionally, physically, all of So at a certain point, I was like, I need to make a change. So I got a different type of job and I became a yoga teacher. I just had to do different things, you know? Yeah. So talk to me about that. You ended up working for some smaller contemporary wholesale companies, first at Ever Clothing, then at NSF.
13:48So talk to me about that transition plus the yoga piece of it. It sounds like it must have been a better fit.
13:55Jamie Haller:Yeah, I think so. The new companies were so different. Like the difference between working at a place like BB and working at a place like Ever is one, it felt really cool to work at Ever and I could pick that color pink in two seconds and move on. I have creative freedom and control and as long as I felt confident and could trust myself and be self-motivated, I could do whatever I wanted in terms of design because they allowed me that freedom. them. Because that's what they hired you to do. Yeah. And so that just felt like an unlock. I just felt like a new person and I could continue being a fashion designer because I was out of the like 28 meetings about one thing.
14:37Jamie Haller:And I just embraced that they were new experiences. You know, when I worked at BB, if you said, I need that swatch and I need it here by nude for my meeting, somebody would get in the car, drive it across town, bring it to you, bring you lunch. Like you had big buying power, right? So you were treated really well. And when you work at a place like a small startup or mom and pop company, nobody's answering your calls. How many pieces are you going to make in production? 50? Well, sorry, you have to become scrappy and you have to work harder. So you have to like get 10 people's jobs done with one person.
15:15Jamie Haller:And that teaches you something totally different. Yeah, I mean, it's resiliency. And also, you know, I think anytime you're put in a situation where you have to do a thousand different things all at once, honing that skill is so important. Like your ability to bounce back, your ability to problem solve, and then how just to execute on things like, yeah, serves you very well as an entrepreneur. Sure. I mean, I was doing every single thing. I wasn't paying the bills, but I was sketching, sourcing, working with pattern makers, creating the line, merchandising, creating the shoots, hiring photographers, hiring models, doing the lookbooks, helping build out the website, learning e-com, eventually learning digital marketing.
16:00Jamie Haller:Like it all fell under the one person that managed creative because there was not that many people. I mean, that sounds like an MBA for starting your own business. Yeah. So you were designing, did I read this correctly, 12 collections a year? Yeah, probably. And that wasn't all the time. But towards the end, yeah, we were doing drops every single month. That's a change based on digital marketing and having a website. And needing newness all the time. Yeah, because when I was at NSF, there was a before having a website and after. And before you just designed for wholesale. And that could be two collections a year, spring and fall, or it could be four collections a year, or it could be four collections a year split into two deliveries per collection.
16:47So it's really eight deliveries a year.
16:49Jamie Haller:And then depending on the health of the company and cash flow, you know, you start doing these exclusive drops because you don't want there to be a drop in cash flow in April. There's these months where it doesn't fit into the wholesale calendar. And I think a lot of companies work this way now. You design for things all the time. So it does change the way brands focus their attention. How do you stay creative and engaged when you are producing at that volume and the need for that level of newness? ideally in the brand you're not designing every single thing new every time right but you also can't show up with the same thing every season buyers have opinions I'm gonna wait and see how that does I'm gonna take a month off I'm gonna wait till I get that tank top before I order another one like that all makes sense so you can't just show up and change the color because that would be boring it's hard and like in my brand now I like to really root a lot of what we do in play and inspiration and doing exactly what I want.
17:56Jamie Haller:I make up the line sheet, but I also know what to put in it. And if I want to do something else that no one's going to understand, fine. Like I do have to keep myself engaged in a fun way. Like we launched the rings and that's just for fun. There's no sales expectation. It's not for wholesale. I'm not going to worry about the wholesale margin yet. You know, like I just want to do things sometimes for the fun of it. Same with the bags, like, because it makes me happy. We'll figure out the business of it after we see if it means something, you know? Yeah. And when I started the shoe line, it was like that.
18:36And I just try to keep wandering and losing myself and inspiration so that I stay fresh. So you talked a little bit about like the buying trips and the inspiration during the corporate days. How did that change during your time at NSF? And then how does it work now today for your own line?
18:57Jamie Haller:Well, I mean, when you work for a small company, there's no budget. So none of that existed. There was no big shopping trips or buying trips. But also on the flip side, it was a lot more rooted in intuition and what I wanted to design and what I felt would match what I wanted to wear. I would lean into my own instinctual thoughts as a designer more. I would be more inspired by fabric or concepts. similar now. A lot of times I'm starting with fabrics or ideas and I don't really do a lot of buying trips. I actually really have become a person that doesn't look at anything. I don't like seeing what other people are doing.
19:36Jamie Haller:I don't pay attention. I barely can like watch movies or listen to music. I can't keep up. The world's really fast. If I look at everything everybody else is doing, that kind of social comparison doesn't make you feel good anyways. You just have to keep your head down and do the thing that you believe in. And I also think that's built on years and years and years of experience. Like you've built the well that you're drawing from. When you're first starting out, you don't have a well. So it's great that you're filling it up with all of these other data points and references and creative ideas. But then at a certain point, it's like the alchemy has to be from you, not just something external solely.
20:16I would imagine. not a designer. Yeah.
20:18Jamie Haller:I think so much of it just comes back to like being able to trust intuition as a designer. And if I'm drawn to something super weird, that's fine. It'll tell me why later. Like it's okay to explore weird ideas. So I want to go back because while all of this is going on and you are having fashion design success, you're also, I believe at the same time dabbling in a totally different space, which is historic home renovation. Yeah, totally. Talk to me about this side of your life and how that started and why it started. It started because my husband and I were both employed, making money, didn't know how to invest it.
21:06Jamie Haller:So we bought a duplex and fixed it up ourselves mostly and rented it out. that was our plan. We're going to buy income property and fix it up and rent it and became landlords. And we did that and we'd do it again. And, you know, we did it so many times that we got really good at renovating and it became very fun. And so then I would, it sounds really crazy to say it like this, but then I wanted to like buy a house because I thought I could buy an old mid-century house and fix it up. And this was like 2013 and we fixed it up and it was amazing. and it was like our first flip that we did. Then kind of the same thing over and over, over years.
21:46Jamie Haller:We're in this other world. It was our side hustle for our lives, you know, like for our investment. And then the projects we would take on would get riskier and bigger. And we were buying hoarder houses and... Oh my God. Yeah. The house we live in in Angeleno Heights was a hoarder house. It was a 1905. It was the first craftsman that I did. It was in 2015 and it was a blast. It was crazy, but like, it was an amazing time. And I think we thought we were going to sell it. And then we loved it and loved the neighborhood and moved into it. And then that neighborhood's full of historic homes. And people have lived in these homes a long time.
22:25Jamie Haller:We bought a few others in that neighborhood. And I just got swept up in this whole like, oh, I love working on craftsman homes. Then was 2019. And we had a big one overlooking the lake that we were working on that we thought we were going to move into. And then I got really nostalgic about leaving the house down the street and we sold it and I got pressed for that house. And it was the first week of COVID. But at this time I had been working on houses for about 10 years. How did you fit that in with your day to day? I'm just working till midnight on kitchen plans and buying tile and looking at Redfin constantly.
23:03Jamie Haller:And I guess it's that thing that's, okay, if I'm going to do all this fashion design and you become a machine on some level, you know, then it's refreshing to look at other things. So it was kind of like an amazing chance to reinvigorate every day was to think about something else. I can see how it would be creatively fulfilling in a totally different way and how the two would probably feed each other because you're looking at color combinations or finishes or whatever it is. And then that sparks an idea for something over here. It feels like even though the worlds are very different, that they would play together in a nice way.
Read the full transcript
23:40I mean,
23:40Jamie Haller:obviously it's all aesthetics at the end of the day, right? Yeah. And experience. Once you've done a foundation in a really old house, then you're not as scared the next time. I also think there's something lovely about it too, because, you know, you think about people do it with their own home and then it's like you've accumulated all of this information that then you don't use again. Yeah. It's almost like getting a kid into college. Like you go through all of that work and then you're like, well, what am I doing with all this information? I worked so hard to get up to speed and now it's useless.
24:08So at least with you, you used it.
24:10Jamie Haller:Yeah. I loved all of it. And I think at the end of my time at NSF, I needed there to be a change again. You know, I was ready to do something else, but I also loved the brand and the team and the people and the stability, I'm sure. Yeah, it was a great job. Plus, being there so long, I could do it very easily with whatever schedule I wanted. Yeah. So you had mentioned that that last house that you sold right as COVID was starting to hit. As 2020 happened and the world shut down, it seems like your own creative world continued to open up in really interesting ways. Talk to me about that period of change and how it led you to shoes.
24:52Yeah.
24:54Jamie Haller:Well, it led to shoes pretty quickly, weirdly. I had like a coffee with a friend who was a shoe designer and she wanted my opinion. She was going to start a shoe line, but she really wanted to be a fine artist. Her family was in shoes. She didn't really want to do it, but she thought, I guess I should. And I went to coffee with her and I remembered thinking and saying to her, like, if I started a shoe line, you have to know exactly what you want. if you're going to start something and it would look like this. And I would do this slipper and I would base it on this thing that I love. And the logo would look like this and the box would look like this.
25:29Jamie Haller:And then I would do a slipper this way. And then I would do it like this on a loafer body. And then I would do a ballet slipper and I would make three slippers. And then I left and I was like, oh my God, that's so crazy. That felt so clear. And the clarity, I think on the heels of 12 years of being a machine, that clarity just felt amazing. I just was like, Oh my God, I'm going to start a shoe line. And then I was like, Oh, that's so crazy. I'm not going to start a shoe line. I don't know anything about shoes. And then when COVID happened, I was like, I'm going to make that slipper. I'm going to make that slipper and see what happens.
26:01Jamie Haller:Like I didn't have anything to lose. It was just something to do something for fun, a way out, you know, talk to me about those early days. Were you still at NSF at that point or had you stepped away? Like set the scene for me. Yeah. Well, I mean, the early, early days of COVID, everybody was on like, you have to work, but we're not going to pay you. You're on hiatus, but you have to keep doing your job. Nobody knew, you know, and it was so scary and companies were going under and it wasn't like I hold that against anybody. It was just the thing that messed me up the most, which was the best thing that happened was I felt very much like nobody cared about me.
26:43Jamie Haller:In COVID, nobody cared about me, which is so stupid sounding, you know, because it's like the world was falling apart. But I just had this feeling where I was like, well, if nobody's gonna watch out for me, then I'm gonna watch out for me. And I'm gonna do whatever I want. I don't care about anybody else. And I'm just gonna say yes to everything that happens. And so when I was introduced to somebody who had a shoe line and I could interview them and that person introduced me to somebody in Italy, I just kept saying, yes. Okay. What's the next step? We talked to a factory. Okay. Yes, let's do it.
27:14Jamie Haller:Okay. I'm going to make one shoe. How much is that going to cost? A thousand dollars. Okay, fine. Let's do it. And then there was some press on the house. I think my domain probably wrote something about it. And then I think Emily Henderson wrote something about it. There was like a few things that hit. Here's the most amazing thing that happened in interiors is every title said how to design your craftsman. And the word craftsman populated an algorithm in Pinterest where like I came up with every craftsman search of somebody buying a craftsman house, they would write craftsman kitchen. And like my article would come up.
27:51Jamie Haller:It was like this weird, perfect storm. God bless SEO. And it was because it was like in Emily Henderson's title. So then people would reach out. My first client bought a craftsman in East Hollywood, Larchmont area, and we're not going to move there. Could you handle like renovating it for us so it's ready to move in when we get there in three months? Yeah, that sounds amazing. I'll handle it for you. Great. The keys are in the lockbox. So sketchy now because from like liability perspective, like all the things, but it didn't matter. Back then I was like, everything's a yes. Oh, you know a contractor?
28:27Jamie Haller:Great. I'll meet him there. It was not professional. But in the beginning, it was like, cool, I'll just FaceTime you when I get to your house from the keys in the lockbox and we'll go from there. Anything was a yes. It's so interesting because it's like you just were pushing an open door. Yeah. I mean, it was a door that you had made and then it stayed open. That's so wild that like this project that you were doing on the side that you had been working on for all of these years. I mean, because you had been building all of this up. ended up being the portal to your independence, even though it was just a hobby on the side that you weren't thinking about in that way.
29:02Jamie Haller:And the shoe thing, you know, it was the same. It was just cool. Okay, I made this Judy slipper. It was like an Indian slipper that I loved so much that I bought in India like 15 years before that. My sister got married there. I used it for every photo shoot at every company I worked for. It fell apart in my hands. I was like, I depend on the shoe. It's like my life. I need it. and I made it. And then when the construction came in, it was like so amazing and comfortable. And I also like collected all these men's seventies loafers. I was like, well, let's take this loafer and put it on this slipper body.
29:35Jamie Haller:It's going to be so good. It's going to be like so soft. I want to wear it, you know, and I made it. And then from that point on, it was just like an unlock. It just like, I don't know, it just happened. So talk to me about actually launching your own eponymous brand, you start going down this route of shoes. At what point do you start thinking like, okay, like let's go to production or I have enough ideas to launch something. Like how do you go from, I want to make one slipper to I now have a suite of options? For the first like year, it was like I made one shoe. I developed my second and third idea over the course of a year.
30:16Jamie Haller:And I just got the one shoe ready. It wasn't hard because I just called somebody, Hey, you want to do a photo shoot with me? I want to shoot this shoe, got photos. I knew how fashion worked. Like I knew that you would email buyers. So I emailed some with the photos that I took and I said, Hey, I started this wine and here's my shoe and by George bought it. And so So that was my first sale. And I was just like, it's an order. So I guess I have to order production. But I guess I just had in mind that like, what's the worst thing that could happen? I could spend whatever this amount of money is, and it could all be for nothing.
30:54Jamie Haller:But as long as I was okay with that, like, amount of loft, that's the worst that could happen. Mm-hmm. So at that point, are you supporting yourself with the design clients and then Jamie Haller shoes? Is that like just the new hobby? Yeah, it was a new hobby. I like to do a lot of things. I wasn't doing it to make money. I was just doing it to be inspired. I was doing it to be lost in something, you know, and doing shoes was very refreshing. I had to learn everything. I was going to say, this is not a category you had been in. That was refreshing. I didn't know anything. So I had to figure it out.
31:33Jamie Haller:I guess I like that. So I was still working at NSF. I didn't leave NSF until like 2022. And that was 2020. Jamie, that's so many jobs you had at the same time. I did. I had three full-time jobs for a while and I had two kids and a baby and it was wild, but it was amazing. It was great. Talk to me about designing the penny loafer, because for anyone who doesn't know, it's one of your main signatures. As you said, it was not your first shoe, but it was a shoe that like really caught fire. And they were recently named Wirecutter's Best Loafer. At what point did you realize that you had such a massive hit on your hands?
32:14Jamie Haller:I mean, to be honest, it's a slow build. It's 2025 now to feel this way. And I started it in 2020. So what makes the loafer and this whole journey really special is that I didn't know how to do shoes. So then therefore I feel like you can break the rules if you don't know what they are. A lot of people would be like, you can't do it this way. And I was like, let's just try it. When you make loafers or shoes, they put these things called counters in your shoes. They basically put cardboard in them. I was like, take it all out, take everything out. I just want skin on skin, like a ballet slipper.
32:48Jamie Haller:And then they're sequettos. So they're, you know, bendy. They're like a little glove, like a pillow that you flip inside out when you sew it. And it creates this beautiful contour on the foot, like bias on a dress. It fills in all the negative space on your foot. And when they sent it to me, the guy was like, do you want seketto construction or do you want lasted construction? And I didn't know anything. I was like, I don't know. He's like, I'll send you both. And when I got it, you just can't unsee the seketto construction. It felt so much better. I was like, oh, well, we're only going to do this ever.
33:23Jamie Haller:But it's harder because it's more expensive. It's a dying art. There's very few factories who want to do it. It takes a lot longer. It's a pain in the ass. That's why people don't do it. It's also more expensive. So I was able to create this thing based on feeling and emotion and without any constraints because I had a full-time job. I made money on homes. It didn't matter if the shoe project failed. And that puts me in a very privileged position, but it's not because I didn't work hard. It's just because it was a hobby. I just was doing it for the fun of it. You know? Yeah. Now it matters if I make money because now I don't have any other income and now I have a staff and production bills, you know?
34:04Jamie Haller:So it's all very important. But back then it was just for the love of it. And every choice was like, nope, that one's better. Let's do that. So there was a moment and I was at NSF and I wasn't secretive. I told my boss at the time I had started a shoe line in COVID, which was one shoe. And he was like, I don't know what you're talking about. Fine. And then I brought it in and it felt like Gollum. I pulled the oxblood beautiful loafer out of the bag and I was like, well, I'll show you guys what I made. And everybody was like, whoa, that's so beautiful. And I was just like, so proud of it. I also had this thing happen shortly thereafter when I was there.
34:46Jamie Haller:And it was like the first piece of real press. And it was right after the Loafer launched. I somehow knew that I had to hire PR. And so I hired PR with like one shoe. And so they got this thing and my phone was like, cha-ching, cha-ching, cha-ching, cha-ching, cha-ching. And it was just like this feeling of like the Grinch who stole Christmas, how his heart just grows. It was this moment where you just felt it happening. And it was like, amazing. Well, this loafer has been a part of my life for several years. I cannot speak highly enough about it. It was my gateway drug. Yeah, that's what I call it.
35:22Yes, it led me to Kitty Points. And then it led me to your Ready to Wear, which you decided to launch in fall of 2024. So how did you know that was the right time? And also, you've been developing additional shoes this whole time. So talk to me about how you were developing that and then how you decided to also get into apparel again.
35:47Jamie Haller:I think the easiest thing for me is to design way too much stuff. I do it every single season. The growth is not by design. It's by accident. In terms of like, I wanted to design 20 pieces, but the lines got 40 in it, but I just can't help myself. It's fun. I just want to play and make and create, and then you have to edit, you know, and I know how to do that too. but I just haven't put any guardrails on. I've just been going by feel and using all that experience to stay the course. I think I needed some space from my fashion designer self after I left NSF, you know, and then I realized I wanted to buy clothes again after COVID.
36:31Jamie Haller:I didn't have any or I was going to have to pay for them. So I might as well make them. That's like such a weird thing. Like if I'm going to buy clothes, I might as well make them. I had a plan. I like talked to my old sales rep who was selling my shoes, talked about this idea. Maybe I would start a denim line, but then I kept adding categories. Well, if I'm going to do denim, I'm going to do a woven bottom too. Well, if I'm going to do that and I'm going to do a photo shoot, I need something to wear. I've got to at least make something for her to wear on top in the shoot. So I was like, I'm going to make a sweatshirt the way I really want to make it.
37:01Jamie Haller:And I was doing it secretly because, you know, my husband was like, you're what? I think I'm going to start a denim line. You are? Are you sure? I was like, yeah. He's like, well, what if it doesn't work? And I'm like, why wouldn't it work? And then I was like secretly adding in categories. And when I launched it, it was like 12 pieces, but I just kind of secretly did all this stuff. And then now it's like 60 pieces or whatever. I don't even know how many pieces it is. It just happened. My 20 years of experience was that. That was the easiest thing for me to know how to do. Well, I have to say, as much as I am obviously an evangelist for the shoes, the clothing has been a revelation for me as well.
37:46I am famously a non-pants wearer, and yet I find myself with a closet full of your pants and jeans. And oh, I mean, the waist tape is like the perfect pant known to mankind. mind, your clothes feel like they're made for real people with real bodies.
38:08Jamie Haller:I'll tell you why. It's because I fit them on myself and I'm a size eight and I have had two kids. I went through those 20 years of doing the way the industry likes, which is you hire the fit model. She's a size 26. She's 24 years old. She looks great. It all looks cute on her. You fit it, you approve it, you get the production in, you put it on and you're like, yeah, I don't want it. I don't like the way it fits me. So when I did my line, I made it so that everything was my size. I love it. Because if at the end of the day, I don't put it on and feel like so happy, then I might as well just close shop because I don't want my name on something that I'm not going to get behind, you know?
38:49I can tell. And it is such a joy. And I also feel like the way that you write both the email as well as the notes on the site around fit about like you can size up in this and it'll look like this. You can size down in it and it'll look like this. You give us permission as your customer to play and to not attach virtue assignment to size. It's wild to me that in such quick succession that you have grown apparel to half of your overall sales.
39:21Jamie Haller:I didn't expect that. When we went to market with the wholesale collection, it didn't exist yet, obviously. You sell it in like February for your August launch or whatever. And I don't remember how many stores we were selling to at that time. Let's say 20 or 25. They all just bought it. And so if it took three years to get from zero stores to 20 stores, and then in the first season, they all bought it. I started at 20. And so then I'm at 20 and 20, you know what I mean? And so it just immediately was the counterpoint and everybody just ordered half and half. and I've just been so grateful to have won over their trust from the beginning.
40:08Jamie Haller:I'd done the startup thing with the shoes, and now I was able to leapfrog over those first few years to it being a little bit bigger from the beginning. Of all of the pieces that you make, like what are some of the runaway hits for you? There are a lot of hits, which is great. There's different things at different times. I'm wearing the weekend shirt. The weekend shirt's been great. I literally wear it every day, though, So that's how I know because I wear it every day. We have a couple different jeans that do great. Like we have one called the Kenneke. I own it. I think it does really well because it's also a shorter inseam and therefore can work for everybody.
40:45Jamie Haller:And then we have one called the crease, which is harder to work for everybody because it's a longer inseam. So you have to commit. You either are lucky and it fits you right off or you maybe have to get it hemmed. But it just looks great. you know, like the butt's really good. You have to like high waist though, but I'm doing it all for me. So I like high waist. So we do high waist. I'm testing new things because that's what you do. You grow and you expand. We did an Anorak jacket and I didn't know how many I was going to sell. They're expensive. I've never sold anything at that price point. So I bought 10 and I sold through the 10 in like 20 minutes.
41:25Jamie Haller:And then we did a pre-order and we sold like 60 in 24 hours. People are like, oh, well, you're not buying enough if you're selling out. It's like, I was never going to buy 60 of this unknown thing. It is expensive. A store buys two. Why would I buy 20? And next fall, I'm not going to buy 60 because that's insane. I'll buy like 20. You have to still be conservative. That's all that experience talking. but it's a great hit. It makes everything so exciting to have all those moments like that. The archive heel was similar. There's a lot of these moments that pop up and it's not everything, but the Navy sweatshirt had that moment last spring and it's continues to be very, very strong.
42:06Jamie Haller:But like, I think we went through three or four reorders where it would just sell out in like an hour. You just could not get it. People were so mad. I have like five of them. Every time I get one, I'm like, I'm just going to take one more of those. I have like a stack of them. So you also this past summer just opened your first store in Montecito, which is exciting for a wide variety of reasons. I can only imagine that you loved using like your full scope of skill set, both in terms of the design as well as actually having all of your designs there. Why did you want to have a brick and mortar store?
42:41Jamie Haller:The truth is I didn't set out to do it. It just happened. Somebody reached out and they were like, do you want to come see what we're doing up in Montecito? And I think I said no, like three times. I was like, I am so busy. Or I said yes. And I would be like, I have to cancel. Like I can't make it. And then I finally was like, I'm going to go see it. And I went up with my CO, Michelle and my husband, we drove up to go see it. And I was like, we're not doing this. I'm not going to get it. I don't have any bandwidth for this. And then as soon as we got there, I was like, oh, we're doing it. Like, I don't even know what I was kidding myself.
43:13Jamie Haller:It was so beautiful. And the way the light kind of dapples through all the trees and the cobblestone. And then like from an interior design perspective, it's like really well done. It's very minimal meets Spanish. It's authentic, but it's like beautiful. So I was like a hard guess and it's in Montecito. So it's like, this is a bathroom. We're going to turn it into a store. Fine. I'll take it. Like I didn't care. I'll take anything. This fall, you also expanded into handbags, two styles, two colorways, right? The ring tote, we did it in two colors and we did the document clutch, which is also known as the bitch bag.
43:49Jamie Haller:I just didn't want to write bitch bag because I was scared people would get mad and I would get banned on social media. And then jewelry too. And we did jewelry too. I love that you're expanding the Jamie Haller cinematic universe. I know. It's fun. It wasn't supposed to come out at the same time. The bags were just like three months late. So it came out in the same week, which is crazy, but I didn't want to wait. And perfect for holiday. Can you tell me what you're thinking about for the future? Is there other newness on the horizon for 2026 and beyond? What I really do want to do is stabilize my infrastructure, meaning like hire more people, give myself some more support, get a little bit more breathing room, do the things I want to do really well.
44:38Are you going to take investment?
44:40Jamie Haller:Well, I'm not at this time. Maybe, maybe I'll have to. I don't have to right now. I love my freedom. I love my creativity. I don't really want anybody to tell me what to do or to report to anybody. I think the magic is just doing that thing where I just follow the love of what I'm doing and find the magic and all the things I want to create without it being that yet. It could be that in time it goes there. But right now, I'm not really worried about that at all. Also, the longer you wait, the more leverage you have. So there's no harm because you're building something amazing. And to your point, you don't need it.
45:20So keep going. Yeah, I feel like we've got a good stride.
45:26Jamie Haller:I don't think I'm going to start like another new category next year. But you know, who knows? I don't even know what I would start. Maybe I would start a home line. That would make a lot of sense. But also, I'm not doing it right this minute. I don't have bandwidth to do it right this second. I don't know. You seem to keep finding it. Okay. So on this podcast, we ask the same final three questions every time. The first one is about mistakes because everyone makes them throughout the course of their career. We don't always talk about them, but I think it's important because it reminds women in particular that you can make a huge mistake and come back from it and that your career has resiliency.
46:08I think those stories are important to hear. So I'm hoping that you can tell me about a mistake that you've made at any point in your career and what you've learned from it?
46:17Jamie Haller:I make mistakes all the time and they're not always my mistakes, but mistakes happen in the company and a product will be wrong. And I tend to be such a stickler for it being the way I want it to be. For example, there were these shoes and they got cut in the wrong suede, right? And the easy thing to do would be just to put them out into the world because probably no one's going to mind. But it bothered me so much that it wasn't what I wanted that I wasted a whole lot of money and recut them in the suede that was like the wrong color. And it's not my mistake, but I really want to do the thing I believe in.
46:55Jamie Haller:And for me right now, it's so important to put my money and my business where my passion is and to be able to stand behind it. So whenever I make a mistake, like even if I lose money, I feel the best about just doing the like thing that's most honest for me, even if I lose money. So like, that's just how I'm approaching a lot of things. I'm trying to just accept that I make mistakes all the time. We all make mistakes. It's just like being kind with yourself and doing the thing you believe in. So a lot of the folks who listen to this podcast are in their first lives and they want to do something different.
47:32Maybe that's staying in the same industry, but going to a different type of company. Maybe it's starting their own company within the same industry. Maybe it's making a huge, total, massive pivot, but they're scared. What advice would you give someone who's thinking about making a change, but just hasn't done it yet?
47:49Jamie Haller:I would say break it down into small steps, right? Like when I started the shoe line, it's like, what's the worst that could happen? What's the next step? Okay. I call this person and talk to them. Okay. What's the next step? Okay. I'm going to call the factory. And then there was a point where it's like, okay, I'm going to place an order for production. It's going to cost$10 ,000. Okay. Take the step, jump off the cliff, just do it, you know, but break it into small steps so that you can digest them. Because when it's the whole thing, if I said, I'm going to start this line, I'm going to hire all these people and I'm going to have this and this and this and this and this, that would be paralyzing, you know, But like calling somebody wasn't paralyzing.
48:27Jamie Haller:The next right step. So my last question is my favorite, which is if you could get in a time machine and go back and speak to your younger self and give your younger self some advice, what would you say? I think I would just say like it's all going to be worth it. You're on the journey. You're in the right place. Everything you're doing is exactly right. There's no exact path. You know, like everything I've done has kind of led me to where I'm at. So then you just have to be grateful for every good and bad thing you're going through. I love it. Well, Jamie, thank you so much for taking the time to chat with me.
49:03As you know, I am a big personal fan and client. I'm so excited to get a chance to sit down and talk to you, mostly because like you really are responsible for like my most worn parts of my closet. And I just can't thank you enough. That's so, so nice. Thank you. That's so nice for you to say that.
49:33That was Jamie Haller. For more inspiring interviews with women like Jamie, head on over to secondlifepod.com where we have so many more for you to peruse. Please subscribe on Apple Podcasts or Spotify or wherever you get your podcasts. And don't forget to rate and review us. we love seeing you spread the word on social and now you can tag us in your posts we are at second life pod on instagram twitter and facebook we always want to know who you're interested in hearing from on the show so send in your requests to hello at second life pod.com or you can dm us on instagram i'm at hillary kerr the show is at second life pod our dms are always open i'm hillary kerr and you've been listening to second life This episode was produced by Hilary Kerr, Summer Hammeris, and Natalie Thurman.
50:25Our production assistant is Raven Yamamoto. Our audio engineers are at Treehouse Recording in Los Angeles, California. And our music is by Jonathan Leahy.
From the publisher
Before Jamie Haller launched her namesake shoe and apparel brand, she worked behind the scenes in the fashion industry in corporate retail. In the 2000s, she designed pieces for big brands of the era like Wet Seal, Guess, and Bebe. After learning the ins and outs of fashion production at a macro level, Haller left the corporate world to work for smaller brands where she had more creative control over her work, allowing her to hone her style as a designer. During the pandemic, she wanted to venture outside of what she knew and landed in a different realm of design: home renovation. Her eye for fashion translated well in the world of interiors, allowing her to gain clients quickly and make a name for herself in the space. Haller’s love for trying new things also led her to a new category of fashion she hadn’t yet conquered: shoes. In 2020, she launched her namesake shoe line and released her now-famous penny loafer style that has become an everyday staple for countless fashion insiders. She later returned to her roots when she expanded into apparel with a line she created with women like her in mind. Today, she’s brought the many skills and talents she’s acquired over the years together with her first storefront in Montecito, California, where you can shop her brand in an intimate space she designed herself.
