Personal Style Expert: How To Dress To Earn More! (Stop Making These Style Mistakes)

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1:26narrative. You might as well control the conversation. In that conversation, I'm going to sit down with Cass, ask her all the questions that we all want to know about when it comes to how do I make sure that I am authentic in the way I present myself? What are some of the tips I need to do to make sure that my wardrobe fits my personality and who I want to become? I can't wait to sit down with her. Let's jump into that conversation right now.

1:53Welcome back to the $100 MBA show. I'm your host, Omar Zinhome, where I deliver practical business lessons three times a week, Monday, Wednesday, and Friday to help you start, grow, and scale your business. If this show has helped in any way, it would be amazing if you could drop us a quick review on whatever app you're using to listen to this podcast right now. It helps me and my team bring new episodes every week. And more importantly, more entrepreneurs will be able to discover our podcast so you can help someone else start their journey. Thanks so much. Sandra Sadie, thanks so much for sitting with me today here in Tokyo, Japan, as Nicole and I celebrate our 10-year anniversary.

2:35Congratulations. Thank you so much. No, but it's great to sit down. And I've been wanting to talk about this topic for so long. So I want to start with like an honest question, okay? I feel like entrepreneurs fall into two categories. The entrepreneurs I see in the world, they're either like hoodie billionaire or their conference speaker from 2007. Why is style so rare? Why is the bar so low when it comes to entrepreneurs? That's a good question and something I ask myself every day because I think style is one of the most visual things that you communicate to the world. And it amazes me how entrepreneurs will spend$50 ,000 on a new website or on a brand deck, but then they will forget the most visual thing, which is themselves.

3:26So I think that in America, at least, it is not okay to say, I want to look good. And I think there is a lot of people look down on that, whether it's with fitness, it's with style. And so for men in particular, or women to say, like, I want to look good. I want to dress well and feel good in my clothing. People dismiss it because they think it's not important. It's frivolous. It's all about vanity when it's so much deeper than that. Yeah. So where do you think that comes from? Like, why do they feel like this is a shallow thing? Honestly, I think it's because clothing has got a bad rap in America.

4:06I have been traveling for the past few months and experiencing other cultures. And it is so amazing to me, like in Europe, for example, it's a part of growing up that you experience nice clothes, that you mend them, that you talk about style and you take pride in that. And I find that's kind of missing in America right now. And it's a lost art form as well to appreciate clothes and to take care of them and your parents as well. I know the Italians have a saying, when you go out to see the world, the world sees you. I think about that a lot when I go to the airport and people are wearing pajamas.

4:42Yes. Like, what's up with that? Like, why are you showing up to the world? Not your best self? Yes. Like, is it comfort over everything? Like, especially when it comes to somebody who has a personal brand or represents a company. Why is this like there a disconnect here? Like, why are we not making an effort? Yes. Well, I think one of the biggest misconceptions that I see as a personal stylist is people think if I am stylish, I will be uncomfortable. and it's just not true. Those two things can live in parallel and be complementary towards each other. It's just that the fashion industry is a business at the end of the day and they want to confuse you.

5:24So you buy more and you fill up your closet and it's just a never-ending cycle. Okay. So you talked about what you do, but I want to kind of back up a little bit. What do people think you do and what do you actually do when it comes to the work you do with people and entrepreneurs? Yes. So most people think that stylists shop all day and that's all that we do. And in stores, online, it's just about clothing and outfits and shopping and spending people's money. And it's not that. I was just telling you before we got on cam that there's so many layers deeper to style. And that's what I find fascinating.

6:00So what we do as stylists at Next Level Wardrobe is we really personalize the service. We ask a lot of questions and we listen to what our clients say because we never want our clients to feel like they're wearing a costume because then they're not going to wear the clothes that they bought. So it has to be authentic to them. And again, that comes through asking a lot of questions and listening very carefully too. Dion Sanders. I know he's not known for style, but Dion Sanders has a quote that I love. and it's if you dress good, you feel good. If you feel good, you play good. Who's a football player.

6:35So if you dress good, you feel good. If you feel good, you play good. When you play good, they pay good. Yep. Right. Is there a correlation like what Deion Sanders has with football and dressing well and all that kind of stuff with entrepreneurship? I agree completely because at the end of the day, whether you own a company or not, you are your personal brand. You are selling yourself. Everyone is in the business of selling themselves, whether you have a boss or you are your own boss. And I think people forget that. Like they fail to see themselves as a personal brand. And so a part I always say a good, a great, memorable personal brand should touch all the senses.

7:15So what you say, how you smell, what you wear. And clothing is so important in that because you can be so successful, have a multimillion dollars company. and then you walk into a room and you don't command the room. People don't look up from their phone. And so building the personal brand is so important. And it's something that is relatively easy to do. I think a lot of people make it out to be a lot harder than it has to be. Okay. So let's say I'm sold. You know, I hear what she's saying. I'm sold. I'm going to do better. I'm going to feel better if I get my style in order. What is the resistance?

7:52Why do people say like, okay, I don't actually do this. I don't actually seek out somebody like Cassandra. Like what's stopping people from leveling up their wardrobe? So number one, most recent one is AI. People think that they can go on ChatGPT and type in a few little lines about their lifestyle, and then it pops out this whole new wardrobe plan. It doesn't work because it's not completely personalized to them. And there's so many layers to clothing. There's seasonality, there's fabrics, there's color combinations that have to be considered. So that's one. The second thing is we work with a lot of clients who are in body transition.

8:31So they're like, I'm going to gain weight or I'm going to lose weight and I'll wait until X date. And so that really becomes a roadblock for them. And so we've worked with clients, executives who have been on this body transition for years or even decades. And finally they get to the point where they're like, okay, now is time. Like I need to do this. So there's a lot of roadblocks out there. The third is a fashion industry because it wants to confuse people. So they buy more, fill up their closet. So there's a lot of things working against people in terms of making it easy to update their style.

9:06But we're all about just keeping it simple and implementing a system as well. I can imagine that because if it's not simple, it's going to be hard to maintain. It's going to be hard to kind of know what to wear every day you know we we talked before we started rolling about even the last couple years i'm a little bit more aware about how i dress and how i present myself but i think that more importantly i i'm thinking more about how do i feel when i dress a certain way versus another way you know when i whether it's it's not even about looking in the mirror it's about like how do i feel in this club like what am i acting as in these clothing yep i find a lot of the entrepreneurial friends i have they still dress like they're in university like a freshman in college or something right yep why do they just kind of stick with that style it's almost like you know i look at my dad my dad i love him to death but he dresses like he's still 35 like he's just that's when he stopped still wears the cargo pants with the sneakers and um the nautica shirts and yeah you know the polos and he actually looks pretty good for somebody was 82.

10:10But why do we as people just have a time in fashion where we just stop evolving? Yeah. I think one, what I just said. So it's like, there's so many forces working against you to update your style, to have it be fun and easy. So that's one. And two, I think people just look down upon it a lot. They think it's going to be a lot of money. It's going to take a lot of time. they think of what could go wrong and they don't think about what could go right. Like, how would it feel if they were to pack in a carry on every single time or to walk into a store and be like, I need one Navy sweater. They buy the Navy sweater and they leave.

10:50So they don't even know what's possible, but they're swirling around in this world of I can't, I can't, I can't. Right. So I'm going to give you the reverse argument. Okay. As you know, we had a software company for 10 years. In the tech world, there's this whole idea of like minimizing decision fatigue. Yes. A lot of entrepreneurs are like, I'm going to minimize my choices in life so I can focus all my thinking and creativity into my business. So I'm just going to wear jeans and a t-shirt every single day, or I'm going to wear that hoodie that's issued by the company that has my brand on it. And that's my uniform.

11:24And I'm not going to expend any energy on the way I look because my product is the most important thing. Why is that wrong if it is wrong? I think there's seasons of life, right? I think a lot of the clients that we work with are executives, CEOs, C-suite, and they spent a good portion of their life going after their goals. So they wear all the hats as a parent, as a partner, they have professional goals. And so style is one of those things that gets pushed to the side really easily. And not for years, I've seen decades. And the problem is you get to the point where then you start running your own company, you're leading boardrooms, et cetera, and you look like you have just started your career.

12:06So your style is not aligned with your success. There's a disconnect happening. And even though people may not be able to articulate what's going on, you can feel it when you see someone who is so successful, but then their style is not aligned with who they are and their success. So it's important to really, you know, your style is going to evolve. So after that season of all birds and free tech fiddies and jeans, then you get to the point where what do I want to communicate? You have gotten to that point of success where you're like, who do I want to be in my clothing? And it can actually be a really fun experience and a really rewarding experience too.

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14:55And let me tell you about Business Plus. It's a game changer. With Business Plus, you can access the top 1 % of talent on Upwork. And with AI-powered shortlisting, you'll get matched to the right freelancer in under six hours. No endless searching required. Visit Upwork.com right now and post your job for free. That's Upwork.com to connect with top talent ready to help your business grow. that's upwork.com upwork.com I have to say that it was a fun experience surprisingly fun when I went to see a stylist and she helped me shop for clothes and all that kind of stuff and I thought it was going to be intimidating I thought it was going to be like I don't know hard like difficult and I think it's the only reason I thought that because I didn't know what to expect yeah right what would somebody expect if they're on this journey, that first meeting with you and they're like, okay, here's my wardrobe.

15:53Like, this is what I wear every day. These are my values. This is what I do. Help me. Yeah. So I think of a great stylist as a coach. So you hire a personal trainer, you hire a media coach, and a stylist is just another one of those types of coaches that you hire and work with. And so I think first and foremost, bucketing them as a coach versus something that celebrities only do, or it's too frivolous to hire a stylist can help. I think from there, what happens with a good stylist is that we really take you through a journey. And so we slow things down. We ask a lot of questions. And when I say a lot, I'm talking like hundreds of questions to get to know you because we never want our clients to feel like they're wearing a costume.

16:40And so from there, that's when the personalization begins. And so we understand your lifestyle, your preferences. Do you travel a lot? What do you do on weekends as well? Do you have small kids? Because if you have small kids, we're not going to have you, you know, spend in high quality clothing all the time. We're going to do some lower price points, higher price points. So the personalization is really important. A great personal stylist will ask you a lot of questions too. Okay. How was that experience for you, by the way, with a stylist. And why did you decide to hire a stylist? Well, I was aware that I'm on camera a lot more.

17:18I'm trying to grow our media company through different channels, social, whatever it might be. I wanted to control the narrative like we spoke about earlier. I want to control the narrative of how I present myself when I go out in the world. And I realized because my life was going to be documented so much that it would just be easier if I just instead of dressed up for a shoot just dressed like that all the time yeah so i i kind of rationalized it in my head i kind of like kind of convinced myself this is actually a practical decision yeah and then when i went through the experience itself i thought oh this is quite easy because a lot of the heavy lifting was done by the stylist you know ask me for some questions what i'm looking for i had a concept of what i like the style i want to evolve into and then pick some pieces out no that doesn't work okay we're going to need to like tailor that a little bit bring that in i think in a weird way it encouraged me to continue to invest in my health and wellness because you always look better if you are fit and you're you know keeping in shape and the clothes just look better when you're doing that especially when you're in clothes that actually fit you and sizing's right and they're fitted properly and all that kind of stuff so that was kind of a surprise that was like oh wow like this is actually another incentive other than you know being healthy and not dying early yeah Yeah, yeah, yeah.

18:35And it sounds like the stylist was a curator for you as well. So instead of you walking into a department store, being like, what do I buy? How do I put it together? She probably curated a special package of clothing where you can literally say yes or no in terms of if you like it, if you don't like it. And then she teaches you how to put it together. So going back to the decision fatigue you talked about a few minutes ago, this is one of the best things you can do for decision fatigue because we work with so many clients that have hundreds of decisions every single day. And for us to be like, buy this, wear that and wear it to this event, it's game changing for them.

19:12And so they can concentrate on that speaking engagement. They can concentrate on the sales pitch and not have to worry about what they're going to wear. Yeah, and I find that when you know that part is taken care of, you can really focus, like you said, like you can really focus on the talk on stage and feel confident that like I'm presenting the best version of myself. Yes. And I think that for years I neglected that. I just kind of thought what comes out of my mouth is what matters and the content and how I present and my presence on stage, my confidence, all that kind of stuff. But we talked about earlier, like in the moments of they announce you, you walk on stage, you get to the center of the stage.

19:51Those are like five, six seconds. People are making all kinds of judgments, like just by looking at you before you even open your mouth. This is applicable if you're on YouTube or on Instagram, if you're meeting somebody in person. There's a few seconds before where they're just even subconsciously making a decision. What has your experience been working with clients in terms of like the after picture? What do they experience once they start getting their style on order? and how do they feel and how do they feel like people receive them differently? Yeah, that is one of the most rewarding things for me as a personal stylist, because they go from frustrated, overwhelmed to I got my first compliment in the past year, like today, and it made me feel really good.

20:32Or I had pants that fit me finally, and they didn't feel too tight. Like all those small wins make a difference. and so we have story after story from clients who are just like really feel authentic in their style and that's what great style is about i always say great style should whisper not scream that's a good one well that's a good lead up to a game i want to play with oh okay we're gonna play a game all right so i'm gonna show you a photo on the ipad okay and you're gonna swipe through these photos and i want you to tell me based on the photo and the person is a well-known entrepreneur that we all know okay okay and you are going to tell me if they're next level or they're game over oh okay okay i'll give you a sentence or two to explain why okay okay so you're going to swipe through and you're going to tell me again next level next level or game over and why okay so we're gonna have a little fun and i have not seen these photos by the way and if anybody has any problems with this i'm the one who chose these okay here we go yeah sorry just flip yeah okay cool oh jeff bezos jeff bezos has really some people would say had a glow up i disagree i think he's trying too hard and for a lot of men that i work with that is their number one fear and jeff bezos is the epitome of that now all right Yeah.

21:58So no. So game over. Game over, Jeffy. Okay. Next, Sam Altman. Sam is quintessential Silicon Valley with the free tech hoodie, t-shirt and jeans. And he's definitely wearing Altbirds too. No go for Altbirds. I would say this is a part of his personal brand. If he were to dress in a suit or something formal, it would be weird because ChatGPT is innovative and up and coming. So I think this is a part of his personal brand. So I would say it's next level. Sarah Blakely. Okay. She is one of my CEO idols. And I would say that she has fun with her style because she plays with color. Everything fits her properly.

22:47She definitely has a stylist for sure. And I appreciate that she plays with textures, colors, and she has fun. That's what style is supposed to be. So next level. Okay. oh god where do i even start with this this is just game over are you going to show the picture yeah of course it's alex hermosi oh yeah game over enough said enough said he's very uh in shape though you can tell by his quads very impressive steven barlett okay so this picture of him is on the jimmy fallon show he's wearing a suit and it's a departure from what he wears on his podcast it feels a little misaligned to me and it feels like he's trying too hard in a way so i would say yeah no go okay yeah oprah okay she is one of my favorite style role models because she is very intentional about what she wears And if you look at her timeline of when she had her talk show to today, evolution, incredible style evolution.

23:57I always recommend to study the best when it comes to style evolutions to see kind of what you want your style to be. I love how she's playing with proportions, with silhouettes, with colors, with up and coming designers. So she is next level to me.

24:16Ramit Sethi, he is so stylish. He looks really good. One of my favorite things about styling him is the evolution that I've seen him go through. He really has fun with his style now. And one of the things that we are experimenting with is wider pants. Okay. So he was a tapered guy for a very long time, tapered pant, and now he's into the wide pants. So we are really having fun with that. And what were some of the like the positives that came out of his evolution oh um i would say a curiosity from him in terms of wanting to know more about how do you put outfits together and what do you think would be best for stage or podcasts etc and when i think about his style it's really him now like he has pieces that are like he's known for his sweaters now and his cardigans and that was intentional actually so it's been fun to kind of curate his look and think about okay what do we want to communicate with your clothes and what do you want to be known for as well next level next level thanks for playing along thank you that was fun yes yes and i want to have a little fun with this because i think that sometimes we take ourselves too seriously and but also just through that exercise and a little bit of a game we learn a little bit about how people are perceived immediately you know like as soon as you see a picture of somebody you have all these ideas about them based on how they present themselves you know i saw how you go you know you kind of like lit up when you saw oprah you know and the visceral reaction of other people as well like what is this you know like so i think that we can definitely as a receiver get it but for some reason we don't see it when we're the subject like when we're the person that's actually presenting ourselves and i think that's like kind of a fun exercise even if you want to those who are watching on youtube just watch back and like oh no how would somebody perceive me if i was on one of those slides yeah and i think it's fun to dream with your style that's the thing like the fashion industry does an amazing job at making people play small with their style so what do i buy and do i have to follow trends and can i wear navy and black hair it's like okay let's calm down, let's breathe, and let's start to have fun with your style.

26:39So one of the things I always recommend people do is to create a Pinterest board. So take 30 minutes and just pin stuff you like, anything you're drawn to, colors, silhouettes, whatever it may be, and then step back after that 30 minutes and zoom out and think, okay, what am I going to communicate with these clothing? And you can even ask friends or family, like, what do you think, what are three adjectives that come to mind when you see this board and then that will put you on your style evolution yeah and if that's too complicated what i find is just easy is to create like an album on your phone and just take photos of things that you see i remember nicole and i were i think we're at a train station or airport and she was looking through a magazine that they had there and i saw a picture of an outfit that ben affleck was being interviewed and he was wearing this like outfit it's like a 70s s kind of sweater blue pants combinations like I don't know why I like this, but I like it.

27:33I'm just going to take a picture of it so I can analyze it later. You know, and just have that mindfulness of like, you see something that kind of resonates with you, take a photo, put it in the album, and then figure it out later. Yeah, that's so important because style is so visual. Like, it's so hard to be like, I like blue sweaters if it's not in front of you. Like, you really have to start signing visuals to it so it becomes alive and exciting too. I want to talk about the psychological side of leveling up and wearing clothes that maybe have people perceiving you as somebody that's established financially has it together because i know that was a resistance for me because i grew up my parents were immigrants we grew up lower middle class i was probably the poorest kid in my high school i went to good school but i was not doing as well in the fashion department as everybody else and i had blessed my parents they tried the hardest and i'm actually so happy that I grew up in the environment because I have some gratitude.

28:27But there is a level of like, this is not me. You know, like, I'm not a fancy guy. I'm not a person that splurges on these things, even though, you know, somebody can be in that position where they can do that. You know, like, how does somebody break these mental models of like, this is not where I came from, or I'm not comfortable spending on myself? Yes. Yeah. And that's a big roadblock a lot of our clients go through as well, because when they come to us, we are the first personal stylist that they have ever hired in their life. And to spend that type of money on a stylist and on clothing, it's scary.

29:03Like, I get that. I think culturally, there are rules of the game, right, that we know and that we're aware of. And with style, it's either like you need to know the rules of the game and decide if you want to play or not. For women in particular, like we get judged more harshly than men on our appearance. I heard your interview with Tina Tower and you were talking about that a lot. And for me, I'm like, OK, I know the rules of the game. I'm not going to change them, unfortunately, but I want to play the game and I want to win. So I think that's a question that a lot of people have to ask themselves, especially if you are a business owner, because you are most likely the face of your brand and you are front and center.

29:47so the beautiful thing about style though is that you can control it and there's so many things you cannot control especially as a business owner as we both know and you can hire a stylist you can hire a personal shopper you can get it done relatively quickly and move on with your life why not play the game and win it why not i like this attitude yeah you know here's the game you're going to participate in it whether you like it or not you're in the world you know so So you might as well learn the rules and when it's your turn to give your best shot, you know? Right. And so the people that say, oh, I could never hire a stylist or I'm not going to update my style because it's just not me.

30:29They should like me for me. That's the game they have chosen to play. And I choose to play a different game and my clients choose to play a different game. And we win because of it. I love that. You want to go for a walk? Yeah, let's do it. Missed calls and slow follow-ups are silent killers for your business. And that's exactly how businesses leave money on the table without ever realizing. That's why today's episode is brought to you by Quo, spelled Q-U-O, the business communication system built so you never miss a call. With Quo, calls, texts, voicemails, transcripts, the contact details, they're all in one clear view.