Business Growth Architect Show: Founders of the Future

Ep #181: Jenny Eversole: What Does a Leader Look Like? How to Nail Your First Impression

• Beate Chelette • Episode 181

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What does a leader look like? How do you nail your first impression? In this episode, Jenny Eversole, founder of Stylespace.com, explains how your personal style shapes how others see you — and how you feel about yourself. The way you look isn’t just a fashion statement but a tool to build confidence, authority, and success.


What if your outfit could quietly speak for you — boosting your confidence, building trust, and helping you lead with ease? 

In this episode, I’m joined by Jenny Eversole, founder of Stylespace.com, who shows us how personal style goes beyond the clothes you wear. It’s an underutilized leadership tool.

Jenny breaks down how your look shapes first impressions and why many founders, leaders, and even corporate professionals unknowingly miss opportunities by not aligning their appearance with their authority. This is not a podcast about following trends, telling you that you can’t be cute. Jenny’s approach is simple, empowering, and designed to help you feel like the best version of yourself so that you can command respect simply by looking great.

If you’re ready to walk into every room with confidence, influence how people see you, and present yourself like the leader you already are — this episode is for you. Watch now, and when you’re ready to take your style to the next level, head over to www.stylespace.com to learn how Jenny can help you stand out for all the right reasons.


Resources Mentioned:

Jenny Eversole: Website | Linkedin | Instagram

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Jenny Eversole:

Hello. My name is Jenny Eversole, and I'm the founder of "Style Space," where we help people look, feel and to present the best, most empowered version of themselves. And on this podcast episode, we will discuss how you can find your most empowered style version of yourself, and how to bring that to your work as a leader, as a visionary and as a Future Founder.

BEATE CHELETTE:

This is the Business Growth Architect Show for founders who don't follow trends. They set them for entrepreneurs who aren't here to fix the past, but to build the future they actually want to live in. Hi. My name is Beate Chelette. I'm a Palisades fire survivor, strategist and the entrepreneur behind a multi-million dollar tech exit Tuva Gate. And every week I bring you the fire, real guests, real strategy and the real talk on how to control your mind move fast and create your future. This is where strategy needs energy, because your next level needs both. Let's grow. Welcome back. This is your host, Beate Chelette from the Business Growth Architect Show, and today I have Jenny Eversole, Founder of the Future, with me, and we're going to be talking about something that I think really needs to be talked about. And that is your style. What do you look like? How do you show up? What other people think when you show up a particular way? The unconscious barriers perhaps that a particular type of dress code may be working in your favors or in your disfavor. And with me, Jenny, you're the right person to talk about this. Welcome

Jenny Eversole:

to the show. Thank you so much, Beate. It's so great to be here. So

BEATE CHELETTE:

Jenny, for somebody who's not familiar with your work, will you please introduce yourself and tell them what you are solving for your clients?

Jenny Eversole:

Absolutely. So as Beate mentioned, my name is Jenny Eversole, and I run a company called "Style Space," and we help people in the workplace and also entrepreneurs show up as the best, most confident version of themselves through personal style. So the problem that we're solving for people, a lot of people, especially post pandemic, were confused about, how do we show up anymore? Is it okay to wear hoodies and sneakers to an office meeting or a client meeting? Everybody else is doing it. Should I do it as well? Or how do I brand myself as a founder of the future, a visionary, someone who is actually making an impact and putting effort into the look and wanting to reflect what and who I am through my personal style, so that those are the things that we are helping people solve.

BEATE CHELETTE:

So one of the things I kind of feel like we need to make a we need to debunk a few of these myths. So do I have a right to express myself any way I want, in the way I dress?

Jenny Eversole:

Yes, of course, you have a right to do that, however, the way that you perceive yourself and other people perceive yourself may not be in alignment, though you may feel authentic and comfortable and relaxed in a hoodie and sweats, other people might perceive that as Wow. They really didn't respect me and my time to show up looking like that, or they probably don't know better, and you don't ever want to be in that position and style, I find it's the easiest way to make an impression like you don't. It doesn't require a lot of education. It just takes a little bit of fine tuning and tapping into the right resources to find something that authentically expresses who you are, but also helps you feel like the professional that you are.

BEATE CHELETTE:

So there's one video that comes to mind, and I even sent that to you, and I shared that with you, and it was this, like, young woman, I want to say she maybe she was 28 maybe 30, and she just had gotten a new job, and she doing this video, and she's crying, and she says she got fired on the first day off the job because she picked what She considered a very cute outfit. And then her boss, a woman, looked at her and told her that was completely inappropriate. And she did this whole thing about on how she was mistreated and misunderstood and all she wanted was to be cute. And then she showed the outfit. There was cleavage, there was midriff. It may even have like a black leather top of some sort, but when I looked at it, I was like concerned that that would interpret a lot of other thoughts other than this. Woman is really professional. How do we maneuver the sensitivity around my right to wear what I want and to be cute, and how do I understand, sort of the larger thing at play, that it is a tool for me, help me to get that straight in my head, because as a part of me, I'm like, who cares? Yeah. And as a part of me, everybody cares what you look like, yeah? Well, for

Jenny Eversole:

sure, so people get called into HR because they are dressed inappropriately. And this is happening a lot with Gen Z. That's just the office siren trend that you're seeing all over Tiktok. And I even was a part of an article in Forbes talking about this as well. So basically, one extra thing I wanted to mention. I have even seen on really big fast fashion retailers, like in the office looks section for women, it has things like this, which I thought somebody who is part of this Tiktok trend must have done this collection, because I don't even know of a profession, like any type of profession, where you would wear these clothing, like not even a cocktail waitress would wear something like this. So my point of telling you the story is we have to not dress for retailers or tiktokers. And a lot of those people are reenacting trends and they're not actually working in an office place. They have been influencers for their whole career, and they don't even know how to dress. So don't dress for Tiktok trends, and don't dress for these fast fashion retailers that are telling you that this is appropriate. So it is a huge underutilized resource to not take advantage of style as a tool, to have people take you seriously, especially if you're entering at 20 years old. I know that when I entered the workplace at 20 I felt so insecure. Had imposter syndrome before we even branded it as such, but I remember using style as a tool to elevate the way that I felt about myself. And I worked in public relations before and I would be asked to do media interviews when other colleagues weren't asked to do the same thing. Perhaps it was because that day, I was dressed in a way that I could show up in the media. Perhaps it was just because people took me more seriously. I'm not sure exactly it's a combination of everything, but it is an underutilized tool to not use style to your best advantage. But if you have to ask, is this office appropriate? If you even have to ask it, you know the answer,

BEATE CHELETTE:

I like what you just said. So let's flip this upside down, right? You know to them that they can dress any way they want, but you're saying it's an underutilized tool. How is it an underutilized tool, and how should they be using it?

Jenny Eversole:

So I feel like sometimes people think of style as an afterthought. They're thinking, Okay, well, I'm working from home. Nobody has even seen me most of the day, but you see yourself, that's one you're also going into the office, or you're meeting with clients, you're going on Zoom calls, and people also see you, even though you're in a casual work environment, that does not mean that a T shirt is going to show the kind of respect to your audience that you are asking for so and it should be the first thing that you think of, because it is the first thing that people see. Within the first two to five seconds of someone seeing you, they're making snap judgments about who you are, whether they can trust you, whether they think you're professional, whether they want to have a romantic relationship with you, and this is all based off of your appearance or your presentation alone. And thank goodness we have full control over our style narrative. We have full control to show people. And it's, it's something that we actually have control over, like, I can't control whether I have sigh, height five, eight or five, two, I can't I guess I could wear high heels or but everybody can control how they're showing up based off of how they put their look together.

BEATE CHELETTE:

So how do we now get this point across? So I mean, in my world, I always felt that I wanted to dress the way I wanted people to see me. I'm really a stickler on understanding personal brand and using it as a deliberate tool, and it changes over the course of your life or career, and so I am not wearing what I wore when I was 30, and I'm definitely not wearing what I wore when I was 40, because, you know, I think that style needs to be evolving with you. So how do I like give us some ideas what is, what is the trick to use this so that I feel powerful and empowered and in charge and appropriate? Are there guidelines?

Jenny Eversole:

Yeah, of course. So I think you have to understand who you are as an individual. Yeah. And who you are as a leader and how you want other people to perceive you, how you want to feel and how you want to be perceived. Those are two different things, but they go together. So for example, last week, I was on vacation in France, and I went to this bakery, and the owner of the bakery, she came out, she was wearing this gorgeous blazer and blouse underneath her blazer, and she looked like an absolute boss. And I said, you own this place, don't you? And she said, Absolutely, I've owned this for 10 years. So the way that I was perceiving her was the boss. Could you imagine if I asked her, Are you the boss? And she's like, No, that's the boss, and it's a person in T shirt and jeans and looking frumpy. Could you imagine how inappropriate that would look and feel to the to everyone in that situation? But she told me the story of her bakery. Everything's handcrafted, baked at the bakery. It was so beautiful, and she was just an embodiment of her work. And she spoke for herself like in her image, spoke for herself too. And I thought, wow, this is the boss, and I felt even better about my purchase because of how she was presenting herself, not just because I think style is so important, but I think everybody needs to think about that woman in the bakery in France. And how do I look like the boss and how do I want other people to perceive me? So the way that I start identifying like, what is my style identity and what is my style brand? I think about three to four adjectives that I want other people to know me by. So for example, one three of my words are bold, chic and original. Those are three things as a leader and as an individual that I want to feel and that what I want other people to see me as. I want people to see me as an original thought leader, and it's perceived there's a lot of ways that you can bring in those three style words. So for example, I always wear color of some sort, whether it's in an accessory or in my blazer, my blazer right now is bright blue, and my earrings, they're gold. They're dangling. They're originally handmade from an artisan in Paris. But everybody has a different interpretation of their style. Word and chic is also really important to me too. Everybody has to define what those three style words are for them, and then how you implement that is, you can take those three style words, go to Pinterest and say chic, bold, original style woman, and then you start pinning all of these different images. That's how you start to get an idea, and brainstorm like, Okay, this works, this doesn't work. And then that becomes your style blueprint, and then you can go to your closet. And of course, the majority I, I'm calling everyone out because I used to be this person too. The majority of Americans, we are only wearing 20% of our closet 80% of the time. And I'm sure that's a bit different for you right now viatta, because you're curative, you're creating a full new look, a full new closet, yeah.

BEATE CHELETTE:

And it's very timely. After I lost everything in the Palisades fire, a lot of people gave me a lot of different things, and my initial reaction was to immediately revert to back to all the things that I had worn before. And I thought, How do I know that's not me? How do I know that what I've been given is not version 3.0 that's emerging? And so I kept a lot more things than I normally would, and it is now six months later that I'm starting to try to try different things. I'm going to give you an example being German and having grown up with a very challenging mother who loved flowers. So we had flower carpets, we had flower wallpapers, we had we had to wear flower skirts. We had to, I mean, flower everything. Neither my sister or I have touched a flower anything since we left home, and I've looked at these women that wear these beautiful flower dresses, and I'm like, wow, I wish I could do that. And then a friend of mine said, Well, why can't you? Well, why can't I? So I have now three flower dresses that I kept, which I've put on and taken off probably 20 times now, because I kind of can't see myself in that. So how do I overcome my own judgment or bias against what fits me or suits me? Because even I know in this case, this is total bias against where I come from in my trauma or background. How do I overcome that and pick what looks good on me without somebody teasing me when I was 12 years 12 years old and never wore anything like this again? Yeah.

Jenny Eversole:

So I feel like we get told. Those stories from the youngest age, whether people intend to tell you this or not or put it in your head. I thought for the longest time that I had the largest ears and that I always needed to cover them up. And it was this jeweler, maybe she was trying to sell me something. Maybe not. But I never wore earrings before because I didn't want to draw attention to my ears. One boy in the seventh grade said, Your ears are enormous. And ever since I've been so self conscious of my ears, until this jeweler said, You do not have large ears, I have seen so many ears you have no idea. And she just validated that I don't have large ears, and they're perfectly fit for my face, and ever since then, I always wear earrings. So I think you need someone to bust those myths for you. You need to take those things and realize they are false, and whether it is a professional stylist that can tell you, No, you actually look good in this particular flower or but I think it boils down to you have to reinvent things too. Like, for example, there's a certain pattern from the 90s and it just, or even from the 80s, like, I just wouldn't touch it, like high waisted pants. I wouldn't touch them because I thought 80s No. Like, we left that in the past, but it's getting thrown back in. And then I realized, wow, these high waisted jeans, they actually do look really good on my figure. I need to just let go of these misconceptions that I've invented myself. So I think you have to be willing to let go of some of those ideas. And there's also a lot of power in reinventing the things that brought you trauma and brought you torment. For example, I hate stinging nettle the way that it hits my hand, like when I go hiking, for example. But I've actually learned you can eat stinging nettle if you cook it and eat the thing that torments you reinvent the thing that used to torment you, because you might find a lot of empowerment out of it.

BEATE CHELETTE:

Yeah, I like this a lot. So what do you what can you share out of your experience are the most common misconceptions people have about clothing or using style as an expression of themselves. What do you see? So a lot of

Jenny Eversole:

people use the word style in fashion interchangeably, when fashion is everything to do with the masses and what style influencers will push on you in the masses to sell things and their trends, and that is so different than style, which is individually curated. It's long lasting, it's timeless, and it's for the individual. So a lot of people think what's in style, but what they really should ask is what style is right for me? Because those are timeless things, and that's something that's individual for you. So rather than looking through Instagram feeds and tick tock scrolls and fashion magazines like you can get inspiration from trends and from like fast like, what is hot and trendy right now, but what is going to be long lasting is what represents you as an individual, and it could happen to be a trend, but most likely it's just going to be something that like a style that reflects you, whether it's a color, a silhouette, a pattern, and those are things that you can style in a certain way to be current and modern. But chasing trends, I think, is the biggest misconception, because then that's how you end up with those impulse buys and tons of clothes in your closet that aren't representative of you, and they may be hot for a moment, or they may never look good on you, but basically you're choosing something based off of other people's opinions and not your own.

BEATE CHELETTE:

How do I overcome that? Though everybody wants that clothes to be comfortable. I want to be cute. But then there's the other thing, I want to be seen for who I am not hiding behind a mask in your work. And I really looking now for sort of experience shares, like when you work with a client, how do you overcome this, or what typically happens, or what are the real reasons of all these excuses really on not wanting to take the time to build your own style? What are people telling themselves and is it true or not?

Jenny Eversole:

Yeah, so in a workplace context, I think people are most resistant to developing their personal style because they don't want to stand out. They want to blend in. They don't really know how to express personality within a traditional workplace context. They and they're afraid. To, like, rock the boat, like I'm talking about women between the ages of, like, 35 to 50. There's misconceptions of, I can't wear this because my body is too this or that, or I can't wear this because I am this age. But your age, your that has the least importance on your personal style. What matters most about your personality, your personal style is your personality. So your look needs to be reflective of who you are as an individual. So it takes a lot of soul searching and work that personal work just to think about like, who am I as an individual, and what kinds of things do I like, and trying things out, and as I mentioned, defining those three to four style adjectives, and start looking around on Pinterest and thinking, Okay, I like this silhouette, I like this color, I like this texture. I'm not a stripes person, but I'm a polka dot person. Or I really love velvet, maybe not this type of velvet. So it's just a matter of experimenting and trying different things on and being willing to prove yourself wrong about what you actually like or based off of what you as an individual like letting go of the expectations of other people and also thinking about specifically the context that you're in. So for example, you can be on a zoom call and you're dressing for the waist up, and the focal point is your face and your shoulders and your neckline. So bringing appropriate things in, like so expressive necklines or shoulder pads, for example, it brings more structure to the look color that compliments your face. Color is really important when you're on a zoom call, because it highlights the color in your face, it will either make it look more faded or it will make it look more vibrant. So thinking about the context that you're in and what you're dressing

BEATE CHELETTE:

for, do you when you work with your clients? Let's give our audience like an example. So my brand at 60 really has changed to, you know, I have to be somebody in wisdom. I have to be somebody who eludes trust, you know, who showcases trust. I want to be. I'm a grandmas. I want to be on the badass grandma. So I like myself a nice leather jacket or two. And so when I start, you know, and I'm a creative so I want that creative aspect, so that I don't look like I'm caught in, in the classic, you know, back in the days business, IBM, blue blazer type of, type of thing, or, you know, the bright red whatever. Not to say that there's not a place for that, but that's not the brand where I'm at right now. You know, I may have worn that a while ago. Now, if I come to you and I say, hey, I really want to do a brand adjustment, so we go and now we sit down, the first step is we say, what are these attributes? And then we're looking at the Pinterest board. And what happens?

Jenny Eversole:

Yeah, so, for example, I was just writing down your words right now, so I would put either edgy or badass as one of the words, as your style, your style adjective. I would also put creative or original as one of them too, and wise or maybe even visionary as one of those words. And then take those three words, put them into Pinterest, and start put in visionary, creative, edgy style woman. And just start seeing what images will generate. And you will start going down different rabbit holes with each image. So for example, you're like, wow, I really love that color, or I love the linen fit of that one blazer. You click on that, and then it'll give you all other suggestions based off of that one. So then you can start collecting images and start seeing parallels between what you're liking. I've pinned 20 images. I must really like flowy structured blazers, for example, or flow flowy structured Blazers with flowy pants like you might find that is you or wow, I really like this color, Orange. It keeps on showing up over and over again. Or I notice leather belts with this detail on it. I noticed that in 20 different images. So keep on building upon that. So take it to 100 images, and then edit back to 20, and then those 20 ideal images, and then start building your closet around that. And you'll get a sense and a feeling of like visually seeing who that person is through all of these images that you're looking at. And as you mentioned, you're literally seeing the future version of yourself. And like what you need to let go of currently in your closet, and what you need to aspire. To be my

BEATE CHELETTE:

style definitely is more a more simplistic style. I do like clean, clean lines. I'm not exactly known to be a fuzzy person in many things. I mean, compassionate, empathetic, yes, but I don't need a lot of these. The thing that I miss the most are a lot of my Robert Lee Morris jewelry, these really beautiful design pieces, which you can't get anymore, because now I'm going through all the photos for the insurance, and I'm looking at what I had, and it's dreadful, because you could wear something super simple and then have one of these necklaces, and boom, there was the focal point. So a couple of other questions. I

Jenny Eversole:

have. One more thing, BEATE, I just think it's the way that you've reinvented yourself in your business after this incident, like this tragic incident, you also have this opportunity to use style to reinvent yourself. You're basically starting from scratch, even though people have given you things. It's sad that you lost some of your prized possessions, but it is an opportunity to reinvent yourself and this new direction. And some like, I know of some clients that they have massive wardrobes and collector items, the fanciest of brands you can imagine that may not even reflect them anymore, but they're just holding onto them because they're like, I can't let go of this is so special to me. I just I can't even though they're never going to wear it, and like literally 1000s or or more of items are in their closet. But imagine if you just lost it all, and you could actually start curating things that you love to wear. So I mean, it's tragic, but it's also like a really incredible experience to be able to reinvent yourself.

BEATE CHELETTE:

Yeah, truly, truly. I mean, that goes back to what you always say, dress for the role you're designing. So what do you think about people that emulate sort of this, Mark Zuckerberg, Steve Jobs, and what was the woman that did Theranos said the black turtleneck. What do you think about people just go, like, I'm just gonna go founder style.

Jenny Eversole:

Okay, well, that is one take. But I feel like you get into, like, a huge risk there, because with everything sounding so similar right now with like the explosion of AI, everything is starting to look and feel and sound the same. And do you also want your look to be the same as these bros or gals in Silicon Valley? When there's so much more you could say about your individuality, you don't want to look like the crowd, and I would say, you can always borrow inspiration from other people. So for example, that is something that Steve Jobs got Issey Miyake to design those black turtlenecks so that he didn't have to make decisions. But could you take it a step further and design your capsule collection, or your capsule wardrobe to be a little bit more innovative and reflective of you as an individual. So I think you can always borrow inspiration from style icons, but just make sure that they're iconic and not super ordinary. Another thing to that I see

BEATE CHELETTE:

the point, yeah, sorry.

Jenny Eversole:

Another reason why that culture persists is that they they feel like they're above style, that they are too important to look and feel and think, and they're like, Well, I am already so successful, and my marriage should be on my work alone. But what if you're not ever even able to tell people the merit of your work because they misjudged you based off of how you presented yourself a networking event, for example,

BEATE CHELETTE:

that is absolutely true, and people may not tell you that, but it is incredibly important, because when you work for Me, you represent my brand, and I need to make sure that if I give you an opportunity, and this circles back to what you originally had said is that you were dressed to be presented to the outside. Yep, 100%

Jenny Eversole:

Yeah. Basically it's a representation of who you are as an individual, your personal brand, the things you value. It is a sign of respect to the people that you work with, the people that work for you, and also your clients that you're serving. It's a sign that you take your role as a leader, as a business owner, so incredibly seriously that you took the time to represent yourself in a very respectful way and also a stylish way.

BEATE CHELETTE:

Well, I think that's a great way for us to end this interview. So what I'm hearing from you is that, yes, I can do whatever I want. Is. The smart thing to do, that depends on whether or not you want to get somewhere, and that depends on whether or not you want to be in control over how people see you. And to me, that's really the most important thing that I'm taking away, that if I want people to perceive me a particular way, I better get good at this.

Jenny Eversole:

Yeah, 100% Well, as I mentioned, it's it's the most underutilized tool I feel as business owners, and it can set you apart in dramatic ways, and not just on how people are perceiving you, but how you're perceiving yourself. When you choose to get up and put effort into your look that represents who you are as an individual, it will actually make you feel more productive, more aligned with the work that you're doing, more confident, more creative and innovative. And these are huge benefits to just deciding to dress the part

BEATE CHELETTE:

beautiful. Thank you so much. Jenny, for somebody who now wants to find out more about your work, or maybe potentially even work with you on whether that's a corporation or an individual. Where would we send them?

Jenny Eversole:

Absolutely so stylespace.com is our website, and you can work with us one on one. There's a section on our website that says one on one, or you can book a meeting with me if you have an enterprise or you want maybe some of your team members aren't dressing the way that you want them to, and you don't want to be that person to say, hey, you know, you could really step this up. You can let us do that for you in a really kind way. And we're all about empowering people with the tools, as I mentioned, like building the mood board and the vision for your style on Pinterest. That's something that we walk people through. We want people to feel empowered, not judged by what they're not wearing or what they could be doing better. We just give people the tools to inspire them to do it on their own.

BEATE CHELETTE:

I love that very much. Thank you so much. Jenny, it's been an absolute pleasure to have you on the show. Thank you for being here.

Jenny Eversole:

Thanks theater. I appreciate it. It's been a

BEATE CHELETTE:

pleasure. That's it for us, for today. So think about this. You know, can you and should you use the way you show up to showcase to other people what's on the inside? That's kind of always how I look at that. And I hope you're taking some tips away. If you know anybody who is a little schlumpy or who might benefit from this, or somebody who is wondering what the best first step is to get themselves more stylish, please share this episode with them, and for any comments, feedback and subscriptions, we, of course, very grateful, and that is it for us, for today and until next time and GOODBYE, that's it for this episode of the Business Growth Architect Show Founders of the Future. If you're done playing small and ready to build the future on your terms, subscribe, share and help us reach more Trailblazers like you. And if you're serious about creating, growing and scaling a business that's aligned with who you are, schedule your uncovery session at uncoverysession.com. Lead with vision. Move with purpose. Create your future.

People on this episode

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Beate Chelette

Host
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Jenny Eversole

Guest