The Who What Wear Podcast: Tibi Founder Amy Smilovic on Why Creatives Should Make "Almost Reckless" Decisions in Fashion, Business, and Life

0:10Kat Collings:Welcome to the Who What Wear podcast. I'm your host, Kat Collings, and today on the podcast, I am joined once again by founder and creative director of Tibi, Amy Smilovic. Amy joins us to talk all about her new book, Almost Reckless, which was released earlier this year. We chat about everything from taking fashion risks and making sense of your current closet to listening to your gut when it comes to personal style. It's all coming up on Who What Wear.

0:39Kat Collings:Amy, welcome back to the podcast. Thank you. So I think our listeners are familiar with you, but just in case, we'll also link your last episode in the show notes. And I was wondering if you could give a little background of Tibby, just a quick overview and maybe the brand's core principles? Tibby's a global brand, independent, always has been. I started it in 1997 when I was living in Hong Kong. We're going on our 30th year anniversary, which makes us officially the oldest, longest standing, independent, largest designer brand in America. So there aren't many independent brands out there. I can say that.

1:20And it really is predicated on ready to wear, sportswear, things that we love. It is a very creative driven company and we show New York Fashion Week and Paris twice a year and that's about it.

1:36Kat Collings:I know it's a show that our editors are always looking forward to each season and we're always like waiting with bated breath to see what styling combinations and what colors you're feeling that season because for us it's one of the brands that can really set the tone of trend direction and always feels fresh and inspiring. And I actually didn't know that fact about the brand being the longest one without the external investment. That's wild and such an accomplishment. Thank you. And the last time you were here in 2024, we discussed your book, The Creative Pragmatist, An Intelligent Conversation About Personal Style.

2:10Kat Collings:And now you're back with a second book, two-time author. I have it right here with me. It's called Almost Reckless. And I wonder if we can just set the stage a little bit for the second book by a look at your first book, Creative Pragmatist, and how you developed that concept. Well, the Creative Pragmatist really came about because I was so frustrated in this industry that demanded that people define themselves in very singular terms. So as a designer, I knew that I was many things and that I could be many things at once, but the industry doesn't really like that or reward that. They need you to be either classic or bohemian or sexy or edgy.

2:51You have to choose a lane.

2:53Kat Collings:You have to stick in it. I always just found it nonsensical when an editor or a buyer would ask me to describe myself. And when I would use more than a couple words, they would always kind of give me this sad little look like, I'll come back to you when you know who you are. And I hated that because I felt like I did know who I was, but maybe I just needed to create the right words to frame that up. Like if you can say it, you can be it. And I get that. I think it is hard for people to really rally behind something if they can't say it, if they don't have a word for it. And so I came up with the term creative pragmatist to describe basically my style that is always grounded in something that is highly creative, but there's a lot of utility, a lot of usage to it.

3:42So it's always pragmatic at the same time. Once I did that, all of a sudden people, the stores, the buyers, the editors, they gave me permission to slide along that scale. And when I would do different things each season that were tethered to that scale, they could comprehend it. They could understand it. I no longer looked all over the place. And the thing was for me, once I created the verbiage around it as well, it really did provide a much more solid grounding for me. So if I look at my life before creative pragmatism versus post, there's just a tremendous amount more of consistency in the design, but not redundancy.

4:24Kat Collings:And I feel like that book is heavy on like the theory of getting dressed and it has a lot of practical tips for how to think about style and express your personal style. And I feel like your new book uses your experience about building and running Tibby as a backdrop, but it's about more than fashion, personal style. It's more like a guidebook that teaches readers how to pursue their own creative endeavors. Would you call it self-help or no? Just like creative pragmatism, I think it's difficult to put it into one category. So I think it's a mixture of business and self-help and probably a little bit of biography as well.

5:00Kat Collings:How did you decide you had this second book in you? You wanted to write a second book. And who are you writing it for? So the reason why I wrote Almost Reckless was to really help people get their gut back or help refine or develop their own gut. And I think this is so critical right now because you're in this world of AI, you are drowning in data, and you've got algorithms that really present themselves with so much certainty that there is, you know, one defined way forward. And I don't believe in that at all. And I think that when we lose our gut and we start to trust only in the algorithm, we start to live life in a rear view mirror, right?

5:44And so Almost Reckless really does help people to first get clarity on what success looks like for them so that they can really drill deep and use the principles of it to kind of serve as guardrails for, you know, building their own path and charting their own course. You know, once you understand who you are, once you've set up your own principles, once you use them as guardrails, you kind of can plow forward at a speed that really looks almost reckless to anyone else, but there's something very settling about knowing different.

6:18Kat Collings:In the book, you describe a style realization you had as a teenager where the trendier pieces you bought that, you know, maybe they fit in with what was going on at the time and maybe got external validation. They didn't align with what made you feel grounded or comfortable. So I'm curious for your advice about how listeners can get a better understanding of whether or not a trendy piece really suits them. How can you tell like a good fashion risk from a bad one? I think you've got to really create your own internal measuring stick for evaluating the decisions that you're making, right? When I defined the way that I design as a creative pragmatist, the step further that I needed to do was to understand what are the qualities in our designs and in the clothing that I wore most often that resonated every time.

7:07And I realized that when pieces of clothing had ease to them, when there was something modern to them, and when there was something familiar to them, they worked for me. But it had to be all three of those things at once. It wasn't like putting on a chill top and a modern bottom and a classic jacket. And then all of a sudden, like it got cooked and became like a cake. Like they exist separately on the body when you do that. So I realized that the pieces that I lived in were always effortless and modern and familiar all at once. Once I knew that that was the benchmark for major success in my closet, then it's something that I apply to everything that I do.

7:54And so if I am looking at a new trend, I try and see it through that lens first, you know, and when I know that maybe a trend is only modern and there's nothing chill about it and there's certainly nothing familiar about it. It's not that I don't buy into it, but I'm going to buy into it in the tiniest way if I'm truly interested in it. What I hear from people all the time, and I know it to be true for myself, is when you start to approach things a little more intellectually, when you really understand if something is right for you or not, it puts you in a much more secure place to decide whether or not you're going to pull the trigger and buy it.

8:35Now that I know what my style is based on who I am, not based on my height or my body shape or anything like that, but based on who I am, then I'm able to sit back and look at a trend often now and appreciate it just as art or appreciate it on someone else. But I don't necessarily have to acquire it because if I do, inherently, I know that it's not going to make me feel like myself. You can be a bit more detached from it.

9:04Kat Collings:It's less emotional in a way. You really just start to even evaluate what is a trend, right? Everything's subjective. Everything comes and goes. First of all, I would never say an oversized blazer is a trend for me because it's the ultimate of chill, modern, and classic. So sometimes people write to me, they're like, oh, are you so worried that the oversized blazer trend will die? And I'm like, I kind of hope it does because then it'll leave the OGers off to their own. You know, you won't see yourself coming and going. I don't think that's a bad thing. There's another line in the book that really stuck with me and like punched me in the gut.

9:36Kat Collings:It's important to lead your life with a compass and not a GPS. This notion is so important to me. And also I think because I've raised Gen Z kids now who were really asked, you know, at age eight, what are you going to be when you grow up? And these were not like fireman questions. Like they really wanted to know what position at Goldman Sachs were you going for? you know with information so readily at hand you know you can type into ai in two seconds right and find out what your path should be if you're eight years old and you would like to work at jp morgan in 20 years right they could they could literally gps set for you if you know which way you're pointed if you know what success might look for you one day to just be happy to be content you start to recognize that like life, nothing happens so concretely.

10:31And if you let yourself be in the moment, you start to do what I call collecting dots. I use an analogy in the book as well, that if you stand up close to a Seurat painting, Seurat uses pointillism, right? And pointillism is just millions of little dots. And up close, those dots look like these blurry figures. You can't make heads or tails of them. But when you step back, the further and further you step back away from a Seurat painting, all of a sudden this whole picture comes into place. And I kind of see life in this way. You've got to collect all of these dots in order to form your picture.

11:13You can't collect your dots if you're not fully present and in the moment. And so when I wrote the book, kind of starting backwards to go forwards, I realized that the things that I've done at Tibby, the gut that I've honed here came from my years babysitting, getting suspended at school, waitressing, bagging groceries, newspaper routes where I had a little smoking section set up at age 11. Like these were all the things that I did that at the time, I don't think anyone could have connected them or made sense of them, but they all played a key role in making me who I am and getting really comfortable with that notion that all of these dots are happening for a reason and that it will ultimately build your picture is settling for a lot of people.

12:06I know I use that word a lot, but there are a lot of people out there who are just very anxious about what's next, what's going to happen tomorrow. And I think being settled and in the flow of things is a really good thing. It clears your head and allows you to make better decisions. Is this a concept that can apply to getting dressed? GPS versus compass? Life principles ground you and your style principles ground you. And so really almost reckless happened as a result of writing The Creative Pragmatist because people were writing me and they were saying, you know, these things that you've espoused for what to do in the closet, they're playing out in my real life.

12:47When I would tell people, when you're getting dressed, make sure to add friction into your outfit because when you don't have friction, things feel dull. It feels really agreeable and it's not giving you any tension. And without that tension, you tend to not have depth. You tend to feel very flat, like you're in an echo chamber. And people would write to me and they're like, wait a minute, I really understand what you mean by adding friction. It's not like just telling someone, oh, dress like Leandra Medin. It's like, no, do this because it actually is the stuff that makes you feel alive and gives you dimension.

13:28And so it wasn't lost on people that that friction that was working in the closet also made sense in their real life. Maybe it wasn't so great to be around people who completely agreed with them all the time. Maybe it wasn't so great to be in an echo chamber. Maybe that feels dull and doesn't excite you. And so it just became a very circular exercise.

13:56Kat Collings:There's also an activity in the book that would be especially useful for our listeners to hear about in chapter three. And it's about making sense of your current closet so that you can set yourself up to make smarter shopping decisions in the future. Can you walk us through that exercise? You know, that exercise was something that we did at Tibby when Tracy, my head of design and I, we had questions ourselves. You know, why did something that we thought that we loved that we sent on the runway not work out for us? Because one thing is to buy the wrong jacket. But if I design the wrong jacket and then I make 200 of them, like I'm really screwed.

14:33I don't want to do that. but I also don't want to retreat to an algorithm to tell me what I should have done. I want to figure this out for myself. And so one thing Tracy and I did at Tibby that I encourage everyone to do in their own closet is we pulled out all the items that we loved. And then we pulled out all the items that we loved and that we personally ended up wearing a lot. Not the ones that sold, I don't really care about that, but what were the ones that Tracy and I wore a lot? And that's where we recognized everything had this ease and this modernity and this familiarity about it. This happened right before COVID in 2019 that we did this exercise.

15:19And that's when I came up with the idea of like, really, if you can distill what's happening in your closet, where you see your most active pieces to three core adjectives, what you're going to find inevitably is those adjectives tend to describe who you are. And maybe not exactly how your friends would describe you, but who you are deeply on the inside. And for sure, I like to think of myself as someone who has a modern outlook and who has the ease about them and who has a lot of respect for knowledge and intelligence and the past, right? Those three adjectives became the way of describing yourself and they became the mantra at the company.

16:05And I started doing posts at the time asking people to come up with their three adjectives. And what was interesting is a lot of the people who followed me on Instagram shared the same mindset and they would write back to me. They're like, well, my adjectives aren't chill, modern, and classic. They are effortless, forward thinking, and heritage. And I'm like, that's chill, modern, and classic. Those are synonyms. You're like synonyms. And so what we realized is all of us in this CP world tend to really intersect on those three things. But we also found that there were things that modified us, that made us different.

16:46Because Tracy and I, even though both of us explained ourselves in those three adjectives, we are not carbon copies of each other. and that was something then that I called a modifier which was a way that gave it that extra twist that was me and for me I always use humor to augment my look if anything takes itself too seriously it really pisses me off and then Tracy had her own modifier and the team members do here as well and that's why we don't look like carbon copies so I think when you get into that in your closet you can go through and discover what those three adjectives are and they have to be adjectives.

17:24They can't be nouns.

17:26Kat Collings:They can't be a decade. It can't be like 1970s. You have to drill to the concept of first principles because the thing about first principles is it can't go any deeper. Synonyms can keep going deeper. They're synonyms. So really, if you can get to that and then figure out what your modifier is, what's that one thing that you itch to do every time, your whole world becomes night and day. It really does. The speed of which you get dressed, the confidence of which you do it, it just changes everything. And you get super good at making decisions super quick. And then it translates into real life. I promise.

18:01You actually get better in the office. You get better at home. You get better at laying down the line with kids or family or whatever. It's a great thing.

18:09Kat Collings:And do you think you can ever go too far, get rid of too much stuff and then kind of being like, up, oh no, I've over cleansed. I think that I would never suggest that someone toss everything out. To me, there's a purgatory place, whether it's a storage place, under the bed, wherever. But when I take those things that are sus and I put them away out of sight, I give it like a year and a half. If I'm cleaning under my bed and I'm like, oh shit, look at these 20 purple sweaters under here. That's when I'm like, I need to call the real real. And if you don't think about them for a while, then that's kind of a sign, I suppose.

18:48Kat Collings:That's a sign. And you've touched on this a little bit, the relationship between gut and data, especially in terms of how tibia has benefited from sometimes moving in a direction that like feels right, even if the data is not backing it up. I'm curious, what advice you would give to any creative about making decisions when gut and data don't align? I assume you're saying, go gut. The one thing that we know for certain is data is pointing you down a well-trodden path. So no entrepreneur, no individual, and I don't think any great business should say, we want to end up like everyone else. That is my goal in life.

19:22Like it might be when you're a 13-year-old girl or whatever. You're like, I want to look like everyone else. But that's not our real goal in life. So for sure, data, the algorithm, it is going to get you where everyone else has aggregated up in mass and has become. And so I would say that the most exciting thing for me is when my gut does contradict the data, because that's your opportunity. That's the white space. Like when you're like, wait a minute, I know this for sure, because I feel it. I am living it and I feel it. And every bit of the data is telling me something different. There's an opportunity here.

20:05Your first book, it talked about how to get style.

20:08Kat Collings:And I think you feel like you're born with it, right? Like you're born with having style or you already know how to listen to your gut. It can be something that we learn, right? Absolutely. And sort of cultivate. So I'm curious how you can tap into your gut. I never was a journaler. But when I wrote this book, I realized that was like, I just crammed like 50 years of journaling into one book. And I think that when you start to kind of write down all the things you felt that you thought to be true, things that you didn't act on that you wish that you had, things that you did act on and that you're so happy that you did.

20:41The act of writing these things out kind of gives you strength because at the end of the day, every decision is ultimately subjective. I mean, unless you're talking about pure math and building a bridge here or heart surgery, Every single thing is subjective. So if you write out what your gut is saying, the challenge then becomes to prove it, whether it's to market it or build it out. But the challenge is to prove it, prove it right, not to have to prove it wrong. That was one of the key things that we went through during COVID when we came very close to shuttering the business, closing it down because we were just so deeply unhappy.

21:28being part of the fashion industry. For my husband and I, in order to really do the hard work to stay in business over COVID, we had to decide what was in it for us. And I kept saying I wanted to be happy. And we had to really drill further than that because that's not like happy giggle, happy, happy, sexy, happy, whatever. For us, we had to drill down to happiness, meaning that we would feel content and feeling content for us meant that we would always be calling our own shots, no matter what. So we would always have agency. It meant that we would always be controlling the creativity and we had to only work with people who shared our mindset, which doesn't mean that you think the same things, but you do think about things in the same way.

22:17You can get lost very quickly. You can get very confused about why you got into this business and what it is you're going after. Before COVID, we thought we were going after being a$300 million brand. And that was what was on the whiteboard. That was the goal. And we realized that everything that we were working towards being a$300 million brand,$150 million brand would come at the expense of every single one of those principles, agency, creativity, and mindset. You cannot have a giant brand and have those three elements intact. I really don't think it's possible, at least not as a pure fashion brand.

23:02We'll figure out if it can be in different ways later on, but not as a fashion brand. All of a sudden we're like, why are we going after 300? We're a$70 million brand. And right now, if we got rid of every single department store and took our volume down to 30 million, we would be intensely happy by this form of measurement. You would have success. We would have success. And that's exactly what we did. We got rid of every single solitary department store. We cut the company in half. And I've never looked back. I mean, I just can't believe that we were chasing after these numbers that were someone else's measuring stick.

23:45Kat Collings:The natural, like more is more, growth is up. Yeah. And you know, like when you're in business, you're like, oh, if a shark's not moving forward, he dies. And I'm like, I don't know. Now I'm starting to think a shark could probably just swim in some circles and have a good time. Maybe. I mean, if there's enough fish around to eat or whatever. The new book and your podcast comes at an interesting time when people, some are feeling disillusioned with work. And I feel like people think you can either have your passions and your principles or make money, but not both. A couple of weeks ago, we aired the podcast I did with Bobbi Brown.