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

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I'm in Tokyo, Japan, and I'm about to sit down with Cassandra Sethi, who is the executive stylist to some of the best entrepreneurs in the world. And we talk about this idea of how do you present your best self?

How do you make sure that that first impression is a good one?

Now, I know a lot of people are thinking, is this superficial? Do I need to really invest in my clothes and the way I dress? The answer is yes, because people will judge you. So you might as well control the narrative. 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.

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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.

Congratulations.

Thank you so much. No, but it's, 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.

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 site or on a brand deck, but then they will forget the most visual thing, which is themselves. So 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. I 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, it's a lost art form as well to appreciate clothes and to take care of them and your appearance 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.

Yes.

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 so you buy more and you fill up your closet, and it's just a never-ending cycle.

Okay, yeah, so you talked about what you do, but I want to kind of back up a little bit. Um, 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. So 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.

Deion Sanders. I know he's not known for style, but Deion Sanders has a quote that I love, and it's, "If you dress good, you feel good. If you feel good, you play good." He was a football player. So 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. So 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-dollar 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? Why 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. So they're like, oh, 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 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, but 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 talked before we started rolling about even the last couple of years, I'm a little bit more aware about how I dress and how I present myself. But I think more importantly, I'm thinking more about how do I feel when I dress a certain way versus another way? You know, when I look, whether it's, it's not even about looking in the mirror, it's about like, how do I feel in this? Like, what am I acting as?

In these clothing.

I find a lot of the entrepreneur friends I have, they still dress like they're in university, like a freshman in college or something, right? 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 the Nautica shirts and, you know, the Polos. And he actually looks pretty good for someone who's 82.

Yeah.

But why do—

like, why do we as people just like 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 so 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, like, 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, they're 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 the hoodie that's issued by the company that has my brand on it, and that's my uniform. And 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?

Mm-hmm.

I think there's seasons of life, right? I think a lot of the clients that we work with are executives, CEOs, those 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, etc., and you look like you have just started your career. So 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 Allbirds and Free Tech hoodies 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.

Hmm.

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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 were on this journey, that first meeting with you and they're like, okay, here's my wardrobe, like, this is what I wear every day, these are my values, this is what I do, help me.

Yeah. So I think of a style, 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. And 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, as with a stylist? And why did you decide to hire a stylist?

Well, I was aware that I'm on camera a lot more. I'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. Like I want to control the narrative of what, 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.

Yep.

And then when I went through the experience itself, I thought, oh, this is quite easy. 'Cause a lot of the heavy lifting was done by the stylist.

She, you know, asked me for some questions, what I'm looking for.

I had a concept of what I, like the style I want to evolve into.

Yeah.

And then pick some pieces out. No, that doesn't work.

Okay.

We're gonna need to like tailor that a little bit, bring that in. I think in, in a weird way, it encouraged me to continue to invest in my health and wellness.

Mm-hmm.

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. And 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. And 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 outta my mouth is what matters and the content and, and how I present and my presence, 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. Those are like 5, 6 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 in 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. Or 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.

Mm-hmm. 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 gonna 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 gonna swipe through and you're going to tell me again, next level, next level, or game over.

Okay.

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.

So, 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, so 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 Allbirds too. No-go for Allbirds. 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.

Okay.

Sarah Blakely. Okay. She is one of my CEO idols, uh, and I would say that she has fun with her style because she plays with color. Everything fits her properly. She 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 gonna show the picture?

Yeah, of course.

It's Alex Hormozi.

Oh yeah, game over.

Enough said. Enough said. He's very, uh, in shape though. You could tell by his quads. Very impressive. Stephen 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. I 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. Okay, to me, uh, uh, Ramit 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, um, 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, 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, on YouTube, just watch back and be 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, uh, 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 together? Oh, it's like, okay, let's calm down, let's breathe, and let's start to have fun with your style. So 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 3 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 I think we're at a train station or an 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 that was like a '70s-esque kind of sweater, blue pants combination. I was like, I don't know why I like this, but I like it. I'm just gonna 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's so visual. Like it's so hard to be like, I like blue sweatsuits. Sweaters if it's not in front of you. Like, you really have to start assigning 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 a good school, but I was not doing as well in the fashion department as everybody else. And I bless my parents, they tried the hardest. And I'm actually so happy that I grew up in that environment because I have so much gratitude. But there is a level of like, this is not me, you know, like I'm not a fancy guy. I'm not a, I'm not a person that splurges on these things, even though, you know, somebody could 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. Like, I get that. Um, 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, uh, heard your interview with Tina Tower and you were talking about that a lot. And, um, for me, I'm like, okay, 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. So 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 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, they 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 because of that.

I love that. You want to go for a walk?

Yeah, let's do it.

Let's do it.

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So we were talking a lot about identity beforehand. I have a question that I know a lot of people are probably thinking in their heads. Kids, do you become the person first or do you dress like them first?

I think you dress like them first and then you become that person. I think it's like we were just talking about your dad, right? And how he was a successful car salesman.

Yeah.

And he would put on his press suit every day, get the manicures, and that helped him step into what he was going to do for the day. Yeah. Yeah, so yeah, I think that's, that's the way to do it.

And I think that even extends beyond just the, the clothes. I, I remember he used to— his car is always meticulously clean, and like, I think I got that from him. My car is always clean inside. And it's like, he always says, like, if you feel good, if you're wearing— your car is clean, your clothes are clean, you just feel like you're taking a shower, a fresh shower, all the time.

Yep.

I think that's a good kind of thought of You can actually produce confidence by dressing in a certain way. So like, if I want to take that first step, how do I have to first identify who I want to become? Is that how it goes?

I think so, yeah. That's the first and most important step, and a step that a lot of people do not do. They rush to buy out— buy more clothes because they think that is going to solve all their problems. It does not. And you really need to slow the process down so you can become intentional. You can do that Pinterest hoard and and then you bring it to life from there.

Yeah, I love that. Um, one of the things that I went through is asking myself that question, like, how do I want to be received? How do I want to be able to show up in the world and become? And it was not like one single idea, it was like a little bit of this, a little bit of that, and this feeling of like, I don't need to prove myself anymore, but at the same time, I don't want to be afraid to dress in a certain way. And it was kind of nice to just express that verbally Yeah, you know, I know, I know that we're talking about clothes and some people think it's materialistic, but it's also a sense of pride.

Yes.

So in that process of asking yourself the question like, who do you want to become, what are some of the things that you have experienced yourself or your clients have experienced where they decide, okay, this is who I want to become, and then that actually manifests by the way they present themselves?

Yeah. So I think of a story of a client we recently worked with, and she is a software engineer leading teams in the SF area, San Francisco area. And before she worked with us, she was very unsure about herself, but she's very successful, and that manifested day to day in her leading confidently. After she worked with us, she— we got an email from her one day, and she said, uh, someone asked me for a meeting and I said no for the very first time. And she's like, I never had the confidence to do that because I was unsure of what I was wearing, how I felt in my clothes, what I was projecting. And it felt really good.

Just to be able to say no.

To say no is so powerful.

I think that's a— just that topic alone could be a whole podcast episode of saying no. But I think there's also this idea of like, I got to start saying no to myself, of like, I can't keep wearing these things, I can't keep showing up this way. And when I say wearing these things, it's more like I kind of see it as like, I don't want to— my external self to not match my internal self.

Yeah.

You know, and I feel like often we deny ourselves that and we just keep doing what we always do because it's easier, like you say, and things like that. So what I want to just continue to do myself and encourage other people that are watching and listening is what are some of the things that you need to start saying no to in your wardrobe? What are some of the things, you know, what does that selection process look like? Is it like something that doesn't give you joy like you hear all the time? What does that look like?

Yeah. So one of the things that fascinates me about style is there's so many layers that go underneath the clothing, and style really uncovers that though. So for people who avoid it year after year, decade after decade, they are not choosing to confront what is really happening for them. And style has a way of kind of revealing what is really going on in terms of how you see yourself. Uh, in terms of no, there's a lot of things you should say no to. Uh, fast fashion is one of them. So no fast fashion. We are at a point where it is everywhere and everywhere. I am so into buying the best, keeping it for a long time, outfitting it in different ways, and really appreciating it. Um, the other thing we should say no to is to follow trends. Uh, going back to what I said, that great style whispers, it doesn't scream. Elevating your style does not mean you have to follow trends or you have to wear bright colors or do something that makes you feel extremely uncomfortable. It is about really owning who you are, knowing what you like and then going after it. And trends usually are the opposite of that for many people. So say no to trends is a big one as well.

Are there any like big no-nos that people should try to steer clear from? Whether it's the hoodie, whether it's sunglasses indoors, like what are some things that people should be like aware, like maybe I should stop doing that?

Yeah. So a lot of people have this thing about getting getting items tailored.

They don't want to do it because they think clothing needs to fit them off of the rack. And I'm here to say, tailor your clothing. Usually it's like a hem that you need tailored, a sleeve you need tailored, maybe the body needs to be taken in. It's so easy. There are many people out there, many talented tailors who could do it. Tailor the clothing. It is so worth it.

Yeah. And a lot of department stores will do it for you.

Oh yeah.

Yeah. You just ask, you know, is this something that they do and they'll do that as part of the purchase.

Yes. Yeah. Do you tailor your clothing now?

100%.

Oh, I love it.

Yeah. Yeah. So a lot of the shirts, a lot of the suits I get, you know, they're not going to fit perfectly off the rack, so you got to get it done. But even if you go to any kind of— not even like super high end, but you go like to like Ross, for example, they'll do it for you. Like they'll just take your measurements and all that kind of stuff. You try it on and they're like, hey, we need to do this, do this. Or they'll tell you straight up like, we can't tailor this to fit you properly.

Yeah.

So you got to get something else.

Yeah.

And the funny thing is about when you buy nicer clothing, you get to keep it for a long time. You're going to take care of it properly. But also, if there is a zipper that breaks or a thread that comes undone, you usually can take it back to the retailer and they will fix it for you. Whereas if you go to H&M or Zara, they definitely are not going to do that. So there's all these benefits to buying higher quality.

Okay, so let's get a little practical. Okay, let's say for example somebody that's watching, listening right now, it's like, I'm going to a conference and this conference is going to be 3 days. Okay, like practically like, how much money should they be spending if they want to show up as their best self in these 3 days? See this as an experiment, you know. Let's just talk about clothing for a moment, just without the advice and the stylist, you know. How many outfits do they actually need? Can they mix and match and save some money? What does that look like?

Yes, so say you were going to a 5-day conference and you need an outfit for the daytime, evening. You could say you need 10 outfits. Now, do you need completely new outfits the whole time? Probably not. But the biggest mistake that I see is people think they need to buy new stuff all the time. So I have, um, people in my community that will see an event on their calendar and they will panic shop. They'll be like, they don't even look at their closet, they run out to the stores, shop online. And I'm like, no, you actually should start with your closet. Shop your closet first, and then if you do need anything, you go out to the shops and stuff. But always, always start with your closet. 10 outfits for those 5 days. You can mix and match. Everything should go together. And another way to kind of elevate your look is to play with accessories. People forget scarves and earrings, and for men, bags and jewelry too, is really— and eyeglasses, sunglasses. Those are areas you can explore.

I was just going to say that everybody that I know that's stylish, like, they leverage accessories in a big way, whether it's scarf or even a watch or something like that. And I think that some people forget about this option even a pocket square or something that just shows a little bit of effort. Yeah. And I think that that's all you need to kind of aim for is like, am I making an effort? You know, because most people don't. Most people just phone it in. I'm just going to wear the Crocs and wear my jeans or whatever and— or my Lululemons and just see what happens at the conference.

Yeah.

Yeah. And leave it up to chance and see what happens. But again, we were talking about when you walk into a room, you can have a presence.

Yes.

Through what you say and all this stuff, but also what you wear. Control it.

Totally.

Let's control it.

Yeah, yeah. Have you ever had a situation where a client just told you straight up, like, now that I've embraced my new style, I'm making more money?

Yes, that has happened. I have had clients with that story. I've had clients who have found a partner because they had great outfits for dates and it led to something more. I have had clients who got promotions as well. It kind of like signals to the universe that I am ready, I am abundant, and I am ready to take everything you have.

Okay.

It's a really amazing signal.

Yeah.

Now we're getting into life advice, but yeah.

No, that's great. That is great because I do think that people think that things are just going to fall in their lap. If I work hard enough, it's going to happen. It's okay to grease the wheels a little bit and make it easier for you to be approach to, you know, somebody come up to you, comment on, oh, I love like a scarf.

What's that all about? Tell me, where'd you get that?

You know, and that can be just the start of a conversation at a conference.

Absolutely.

You know, on the train, whatever.

Yeah.

And again, it's going back to the rules of the game, right? You're either going to play it or you're not and play the game and win.

Yeah, I love it. Do you recommend somebody has like a signature move, a little bit of a flair that's theirs, like they cultivate, like whether you don't have to go to extremes and, you know, wear sparkly socks like Michael Jackson, but like, there's only one MJ. But do you, do you think that somebody should be like, okay, that's your thing, you know, you wear a brooch, or you, you know, like, and just cultivate a signature move?

I love that.

Yeah, I, I really encourage that with my clients in my community because that is what makes style fun, makes your style you. First and foremost though, you got to get the right pieces in your closet, you got to get the right fit, you got to like develop those skills. It's like learning a new language, right? You got to learn the basics and then you can expand to that eventually.

Maybe a beret for me.

Yeah, a beret. Or yeah, maybe earrings too.

I don't have the hair for the beret. Yeah.

Oh, so I have a question for you.

Sure, go ahead.

Who is your style role model? Is there a man whose style you admire, or a woman, or—

Yeah, that's a great question. Uh, that's a great question. Um, probably Probably top of my head, George Clooney.

Oh, okay.

How come?

It doesn't feel like he's trying too hard, but everything fits nicely. He's also not acting like— he's acting his age, you know, like he's kind of embracing the fact like he's getting older and, you know, he's dressing the part a little bit.

Do you have like a signature piece that you like? Like, are you into sneakers?

I'm into sneakers. I'm into socks. I like different kinds of socks. I find it hard to buy clothing in most stores because the style now is oversized, and I don't like oversized. Like, it doesn't look well with a tall person as much.

Oh, okay.

I just don't like it on me. Maybe—

wait, who— do you think that, or did someone tell you that?

I think that. I like it whenever I wear it. I just feel like I'm swimming in it. Like, I don't feel— I think it would look so cool with like an oversized sweater or like oversized pants. And not maybe pants, but the With all your cool sneakers you have. Yeah, I love sneakers.

Yeah, you should try it.

Okay, so we're going to take a moment and not be serious for a second.

Okay.

But also serious.

Okay.

Love it. And I want you to feel free to tell me what impressions I put out there in the world by the way I dress. Oh, yeah. Even what I'm wearing right now.

Omar, put me on the spot here.

You can grill me, you can roast me, you can do whatever you like.

Okay, give me 2 seconds. Okay, you come across very approachable, um, and you have like a nice smile and like grooming is on point. And I think that all plays into like the approachability. Like, like what if I didn't know you and saw you online, I'd be like, I'd want to be that guy's friend. Like, he seems really cool. Um, we were talking about how you like sneakers, so there's like an athletic component too, which is like, oh, I wonder what's behind that. And then I know in some of your YouTube videos you have a record in the background. So your love of music and stuff. So you're warm, you're friendly, approachable. Those are kind of the main words that come to mind.

I like that.

Yeah.

I like the fact that you say that because that's what I'm trying to do.

Yeah.

And I'm actually trying to become the person I needed when I started out in entrepreneurship. I needed somebody to just tell me like, just forget all this jargon right now and all this business talk. This is what matters, you know. And I feel like it's hard to do that if I'm not coming across as like an ally. As I'm getting older, I even call myself Uncle Omar sometimes, like, don't tell— don't tell me that Uncle Omar didn't warn you about this, you know, that type of thing. But I'm glad that I— to hear that, because yeah, that's, that's what I want to portray in the world.

Yeah, I think you do a good job of that. Some— do you want some suggestions?

Yes, please.

So So I think you should try a wide leg pant.

Okay.

And the reason why I think you should try this is because it's just cool. Like you, you have a cool factor about you. Like the athletic.

I can pull it off.

Yeah.

Yeah. So I think you should do a cool wide leg pant.

Like a Japanese style.

Yeah.

All in the right place.

Yeah.

With some cool sneakers I'm sure you have in your collection. You can do like a nice sweater, kind of like jazz it up a little bit more fitted. I think it would look great.

Okay. And do you have any suggestions? Thank you so much. Do you have any suggestions of like, where do I go? What kind of store would have that? Like, what do I— like, I know I'm asking a very basic question, but—

Yeah.

So if you were ever looking for a specific type of garment, always start at a department store because they have so many brands under one roof. So it's kind of— it could be a one-stop shop versus going to boutique after boutique after boutique and hopping around the city. Start with a department store. I'm sure you'll find something.

So I want to push the boundaries a little bit with my style, like, and I'm gonna give you some ideas I have, and you tell me if that's like too much, I'm trying too hard, or like go for it. Okay, okay. So like we're gonna put the wide legged pants in the equation, but like what if like a little bit of a funky kind of like jackets that I would wear to the Grammys or something like that, like something like with bit of, you know, pizzazz, spikes, or maybe like a little bit of sparkle or something like that.

Oh, are you into that?

I admire artists that wear that.

Okay.

I'm like, can I pull that off? Because I love like that piece that kind of, you know, you could be kind of the solids and then wear something like that, and it's just like, okay, that person showed up.

Yeah, I think you should try it. Okay, explore it. But maybe you start with day-to-day wear.

Okay.

So maybe it's like a cool hoodie with some heart underwear on there, like a cool zipper. So you get comfortable with it before you spend a lot of money on like Ed Hardy or something. Yeah, or John Varvatos. Yeah, yeah. So I always encourage, like, you and clients to start small and lower price point because you're kind of trying to figure out if you even like it. Yes. If you like it, if it proves itself, then you go further.

Okay, I'm gonna get even more practical. I know a lot of people, they're not really sure where to shop. They don't know if this is a good idea, bad idea. Let's talk about outlets. Okay, is it a good idea to go to outlets? Are there better outlets to go to, high-end outlets that are worth it, or it's like if it's an outlet then it's not going to be good?

Yeah, I think outlets could be an interesting place to shop, a good place to shop, but most important is you have to have a plan before you shop.

I like that.

Because this is the problem, the biggest problem, the number one mistake that I see is that people don't have a plan. They buy stuff that they don't need and then they don't wear it and then they feel bad about it and then the cycle continues over and over and over. So I'm always like start with your closet, do the edit, assess what the gaps are, create your shopping list. Then you can go to the outlet, you can go to the department store, whatever store is best suited for your budget.

Do you recommend like taking photos of what you in your wardrobe so you don't like— because I, I think a lot of people, including myself, buy things they already have.

Yes, yes, I see that all the time. So a good example of this is for women is black Pants. I see women's closet and they have 10, 20, 30 black pants from the same retailer. They feel like they're buying something new and they get the rush of buying. It's literally the same thing, maybe in a new size or a new fabric. Same, same, same. And there's nothing wrong with having like a few pieces that are the same. When I say a few pieces, like 2 pieces that are the same. But you have to understand what is going on in your closet first and on those before you go out shopping. Same with business, right? Like you would never do a podcast without the preparation. And it's the same thing with your closet. I like that.

I really do. And I think that kind of goes hand in hand with like understanding, like you want to be efficient with what you're spending on, but also at the same time, you don't want to just continue to do the same thing over and over.

Because that's how you get stuck and that's how you don't evolve too. So I always recommend doing a minimum of 2 closet edits a of the year.

Okay.

Minimum. And though that is a real opportunity to be really honest.

Yes.

With yourself.

Try stuff on, have a friend there, a stylist, and get rid of stuff that is no longer serving you. It's so freeing to do that.

It is freeing and it feels like you're taking action. It feels like you're taking control. Uh, Nicole just reminded me recently that I need to do a sock drawer edit. So I think I'm gonna to see which of these socks are over 2 years old.

Yeah.

And then maybe give it to somebody who needs it.

Yeah.

When's the last time you did a closet edit?

Oh, recently. I think it was about 4 or 5 months ago.

How was that for you?

It was great. The best one was like about 2 years ago when we sold Webinar Ninja and I was like out of the software tech world. And when you're in the tech world, you go to a lot of conferences, you go to a lot of meetups, and you get a lot of free swag. And as again, immigrant household growing up, like a free t-shirt's a free t-shirt. I can work out in it. I can use it as a pajama.

Yep.

I can all make stuff.

Multipurpose.

All this stuff, an undershirt, you know, I can do something with it, right?

And I went through my closet and my drawers and I got rid of so many free hoodies and sweater shirts and t-shirts and all this stuff that like, I'm like, I'm not gonna wear this other person's brand or whatever. And I just, yeah, we just cleaned it out. And then I went through like the old jeans and the old stuff that like Nicole and I call the Old Navy days.

Oh yeah.

Like, you know, whereas it's like where you, where Old Navy was an option.

Yeah.

Like, you know, and no, no knocking Old Navy, but it's, it's the lowest form of fashion. It's the lowest form of quality.

Yep.

It's the lowest form of actually that brand, you know? Like it's like Old Navy. Isn't it like Old Navy, Gap, Banana Republic?

Oh, Banana Republic.

Yeah.

Uh-huh.

So we had to kind of say goodbye to the Old Navy days.

Yeah. And you hold your closet to a higher standard. And it's fascinating to me because I work with so many successful professionals of all levels, and they have their life in order. Like, they work out, they have trainers, like, food— everything is dialed in but their closet. And it is wild to me because they're so successful in one area, but their closet tells me so much. It's usually packed, it's usually the same things, and it's like weights that they carry every single day.

I want to talk about travel and shopping because I find that when I travel, I, I find some really good stuff, even just like in the, in the airport. Like, I know, like, there's this like meme online, like, who shops at the airport?

Some of them, some really cool stuff at the airport.

Like, we're in Milan and there's a store called Bocci Milan, like, and it's got some like really cool basics but nice cuts. And I got a jacket there, I got a sweatshirt. And like, it was, it was just like I never considered it. Yeah, but I know I can't find that anywhere else because like it's specific to Milan.

Yeah.

You know, and do you recommend people like to have that like as a part of their itinerary when they go traveling? Like you're going to, you're going to go to Rome, you're going to go to, you know, Japan, you're going to go to Paris, you know, London. Should they do a day of like, hey, explore, buy a piece or two that you might, might work for you that's unique to that area.

Yeah, I think that's a fun thing to do and a fun way to honor the culture that you're visiting. So right now we're in Japan and they have incredible vintage stores here. So do I need anything right now? Not necessarily. But do I want some vintage?

Yes.

And so I've been doing a lot of vintage store visits just to see what is out there. But I know what I'm looking for. So outerwear, maybe some pants, and that's it. So always having a plan before before you go to those stores. Yeah. So important.

My Japan plan is there's a lot of nice vintage watch shops here.

Yes, there is.

Where you can get some really good— like, the thing about the Japanese is that they take care of their stuff. So even though it's, you know, pre-owned, it's pristine. It's like new.

It's crazy. Yeah, I know. Oh, and you have to put wide leg pants on.

Wide legs on. It's on there.

It's on there. Definitely watch than that. Yeah. But I also find that, like, we were at a vintage store the other day And I was looking at the shoes, like there's no creases in the shoe.

I know.

What is happening here? It's literally— It's definitely an old shoe.

Yeah, it's brand new. I've been to a lot of countries, a lot of vintage stores, Europe, Asia, America. Japan has some of the most pristine product that you will ever see in vintage.

Yeah, and I do want to warn anybody that does go to like a vintage shop in Japan, like the price reflects that quality.

Yes.

Like you're not going to get the good will, you know, $5 for a shirt, you know, or like a dollar for a tie.

But even the lower price point vintage shops here, pretty good. Yeah, I have to say, like, very impressive. Yeah, so vintage shopping here in Japan is really cool. But also, I want everyone to know, like, you don't need a ton of money if you want to update your style. You need a plan.

Okay, I want you you, as we wrap up this conversation, to send a message to our listeners, to our viewers that are sold? They're like, I love what, you know, Cassandra said today, and, and I want to get on this journey. What do they need to hear to allow them to allow themselves to go on that journey?

Have fun with it. I think a lot of people forget that style is actually a creative expression. Of you, and it's actually meant to feel good. It's not meant to feel like a chore or a drag or you feeling overwhelmed all the time. So if you start with creating your vision of what do I want to communicate, how do I want to feel, all those high-level things, the tactics will come and you will get there. But form your vision first and have fun.

I love it.

Thanks so much for being here.

Thank you.

Yeah, let's go shopping.

Yes.

I hope you enjoyed that conversation with Cassandra Sethi. I sure did. Now it's time for you to take action.

It's time for you to get your style in order.

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