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Welcome to Styled by Estelle. Hello and welcome to Styled by Estelle with Estelle Winsett. Estelle is a former attorney turned personal stylist who helps women lawyers project confidence, authority, and authenticity through style.
She believes your wardrobe isn't just about fashion, it's a performance tool that can help you show up, stand out, and own the room. I'm Heidi Mack and today we're kicking off this series with a powerful conversation about why your clothes matter more than you think, and how the right style can change the way you feel, lead, and succeed. This is episode one, Power Style, Why Your Wardrobe Is More Than Clothes.
Hello Estelle, thank you for joining us. Sure, I love it. Glad to be here.
Wonderful, wonderful. Let's start with your story here. What inspired you to go from practicing law to working as a personal stylist for women attorneys? It was really kind of an evolution.
So I started off practicing law. I come from a family of lawyers, so I am one of four lawyers in my family, my dad and two sisters and I. And so I just always thought I was going to be practicing law and I did enjoy it. I was a litigator, so I was in court and I enjoyed the gymnastics of law and thinking on your feet.
But I started wanting to have something that was a little bit more family friendly and I was wanting a different environment. And so I landed in legal recruiting and from there I went to career services and professional development all within the legal space. And I started helping women on the side with their style.
It was something that a passion I had that was reignited later in life. And I realized that there were a lot of women out there who really struggled with their style. And for me, it came easily.
And I also realized on the way that it was so much more than style and the clothes, but it was the confidence that women got once they felt really good in their clothes and in their skin. And so what started off as kind of a fun project really became a passion project. And the through line through all the things I've done is that you need to market and position yourself in the best light you can.
And you also get to intentionally create the image and the message that you send to the world. And style is such a powerful tool to do that. So not only does it increase your own personal confidence, but it allows you to communicate who you are to the world and how you're showing up with the way you look, the way you talk, and just your overall appearance.
And so for me, I think that's super powerful. Oh, yeah, for sure. I mean, my grandmother definitely was the one that taught me how to accessorize.
But again, she wore that with confidence. So I totally agree with you. Same, my mom was my first style icon.
She was such a lady. Yeah, she was amazing. Love that, love that so much.
So you did say that the style is a performance enhancer. So what do you mean by that? And have you seen it affect the way women show up at work? Yeah, I definitely think that style is a performance enhancer. And what I mean by that is when you're wearing clothes that fit your body really well and feel like you, so they feel authentic to who you are, then you don't have to think about what you're wearing anymore.
And so many women are wearing things that they're not 100% comfortable with, or maybe it doesn't fit them well. And so they're, in their mind, second-guessing what they're wearing, thinking, I shouldn't have worn this. Maybe they're having a wardrobe malfunction.
I can't tell you, there are so many times where I showed up at a deposition and my blouse was a little bit gaping and I was so self-conscious about it that I was trying to like put my legal pad up here so that you wouldn't look at me, so I wouldn't flash opposing counsel. You know, there's these things that, as women, we think about. And if you're thinking about, oh, I shouldn't have worn this, you're not focusing on your case.
You're not focusing on your argument. So it's taking away from your performance. But in addition to your own thinking and what you're doing, you're also distracting other people.
So if you're giving a presentation and the clothes you're wearing don't fit you well, then you're usually fidgeting or you're kind of adjusting yourself or you're shifting back and forth in your seat because you don't feel 100% confident. And when you do that, you are distracting the person who's watching you. You're taking away from your own sense of authority.
And in essence, you're just limiting your abilities and your performance when you don't have clothes that fit you well and make you feel really good about yourself. Completely, completely. You do that on just a regular date, you know, or, you know, going to dinner with you.
Yeah, so the pressure of that being an actual courtroom, that's added to that. So yeah, I could get that. The other thing that I think is so important is I think women discount how often they're worrying about style.
They think it's not a big deal, but they have an event coming up and they're at lunch and they're scrolling through online shopping, just trying to find something more. They spend an hour talking to their friends, what should I wear to this? I mean, there's so much time and thought that's put into it that women don't even realize that they're wasting this large amount of time and mental energy worrying about something like that. Yeah, see, and like going along with that with professional women, especially in-law, they can feel invisible and overlooked.
That's why we spend so much time in that with style. So how can style help change that? Yeah, so when you're wearing something that fits you impeccably, I think that's one of the best indicators of style is something just fits your body really well. Then you know it, you walk into a room and you really start to own the room because you know that you look the part, you feel really good
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in your skin and it's kind of hard to ignore you when you're feeling that way.
You just radiate happiness and confidence. And conversely, when you're wearing something that doesn't make you feel good about yourself, then it can bring your energy down. It can make you almost shrink because you're not feeling good about the way you're showing up.
And so it impacts your posture and it just makes you blend in more to the background than you already were in clothes that you didn't feel 100% confident in. Exactly. So there is a link between clothing and confidence, as you're saying already.
So putting on the right outfit, that can really shift how we carry ourselves then. Yeah, it really can. If you think about it, when you have had an outfit that you just know, people, women know when their outfit is right.
And it's just this feeling. I'm sure you can think back in times in your life when you just had the dress or the pamp suit that just made you feel amazing. Like a lot of women will say, this is my lucky pamp suit.
If they've worn it in trial, they feel really good and powerful in it. And then at the times when you're putting something on, you thought it looked okay in the morning, but you were in a hurry. And then you get to the office and you're like, I forgot.
This really is not flattering on me. This makes me look a lot whiter than I am. And then every time you go to the restroom and see your reflection as you're washing your hands, oh, I hate this outfit.
And it's just, that's how you start your day. You can either start it on a high note because you love what you're wearing, or you can start it second guessing yourself frustrated and then kind of having a snowball effect throughout the day. So going along with that, for women that feel like style is superficial or indulgent, what would you say to reframe that perspective? Yeah, I would tell them that there's scientific studies that you make a first impression within seconds of meeting someone.
And you only get one chance to make a first impression. And what you're wearing is a big part of that first nonverbal communication. So if you actually think about it in terms of advocacy, your clothes are either advocating on your behalf or against you.
And you want to be stacking all the odds in your favor. So I think thinking it through it as a means of communication and of advocacy is a way that can really help you shift what you think about it. Exactly, exactly.
You know, personal experience, like my best friend has never been really into style like that. But anytime that I've like, let's go, let's go to the store, let's try something different that she's not used to. Like seeing the essence like radiate off her, you know what I mean? So going with that, some people just, yeah, describe it style as a form of self-care.
That's why I try to do that with her too. I'm like, it is a type of self-care. You see it that way.
Maybe, you know, with getting dressed, even for yourself. Absolutely. Yeah, I really noticed this a lot during COVID because at the time I was working at a firm and, you know, everyone was home for once.
And at first it seemed so exciting to, oh, I can wear pajamas all day if I want to. This is great. And of course that lasted about three days and then you're really bored of that.
But what I realized is, you know, throughout the day, even if I saw no one at the firm, I saw myself. And if I hated the way I looked, if I was wearing some old, you know, sweatpants or something that wasn't flattering and hair on top of my head, I would just be like, oh, you know, you just see yourself when you know you're not dressed apart. And then that just makes you feel bad about yourself.
Whereas if you actually take the time to put on an outfit that you feel good in, that you feel like it's flattering, then that's going to start your day feeling really good. And every time you see yourself, you're going to feel good about it. So it's not necessarily about seeing other people.
I mean, there is that message of what message you send to others, but there's also the internal message that you send to yourself, you know, that you're worthy of getting dressed today in a way that you feel good in, regardless of what you have to do for the day, but really just for you so that you can feel good. And that's one thing. That's kind of why I really, really focused a lot on, wow, this really is self-care to give yourself that time to get dressed in the morning and to wear something that you know you feel good in instead of just grabbing the same three boring outfits that you've been wearing on repeat.
So that was before this podcast, you know, I'm like, I put on my outfit for the podcast and I'm like, oh, hey, I feel better. It's true. Yeah.
Yeah. When you said the hair up and some sweatpants, I was like, oh, that was me a couple hours ago. I was just describing myself as well.
I'm very familiar with the floppy look. I can do it very well. And now see, and now we're talking about sweatpants.
That is an easy thing. And it goes with our, you know, next is like we delay buying clothes sometimes, like until we lose weight or we deserve it. Why is that mindset so common? It's, is it damaging? It's very damaging.
And I talk about this a lot when, and I've done it before too. I think as women, a lot of us have done this. And what we're end up doing is we're punishing ourselves.
We're saying when I lose 10 pounds, then I'm worthy enough to go buy clothes for myself. But you still have events to go to. You still have things where you need to be dressed.
And so you're showing up in something that you're either squeezing yourself into that's way too small, that physically feels uncomfortable and that you don't feel good in. Or you're hiding in something super oversized. I think women, we tend to do one of the extreme, like just keep wearing the thing, even though it doesn't fit or just hide ourselves so that you don't see any shape.
Neither of which is flattering
and both of which make us feel bad about ourselves. And so I like to shift the narrative when it comes to that as, you know, you're worthy now. You don't, you're not going to become more worthy if you lose 10 pounds.
And I think part of what we are dealing with as a society as a whole, I mean, how many times do you hear, oh, is she going to bounce back after she has the baby? Like, I think we keep thinking that we're supposed to always be the same size we were in high school, which is so unrealistic. And if you think about the hormones that we go through, our bodies shift. I mean, you know, puberty, pregnancy.
I'm now in perimenopause where it's like things are shifting again, you know, and we're not meant to stay our high school body shape. And there's no world failing if we aren't. And I think just accepting where you are is really empowering and finding clothes that fit you now and that flatter you now.
And if you lose the weight, great, but don't punish yourself now in the interim. So like in your work with your clients then, what kinds of transformations have you seen when someone finally embraces a style that feels like them? It's just, it's really why I do this. I was thinking about one of my clients who came to me early on and she was a mom of two and she was also a partner at a law firm.
And she felt like she really didn't have anything of her own, you know, because she was either in mom role or she was in partner role, but she really didn't have something just for her. And so it's almost like our sessions were her time for herself, like that self-care we were talking about. But also she looks kind of young for her age.
And I talk a lot about when I first started practicing law, I looked about 12 and that did not help me feel confident as a lawyer. And so I understand not looking old enough to be the part and how that can be really damaging because people don't think you have the experience that you do. And that's really frustrating.
And after we worked together, she was, you could just see it in her face, just lighting up. She would send me text messages, you know, she showed up to some meeting and the other attorneys were like, well, look at you showing up and in charge, you know, and it's just that whole attitude that others notice too. And she started having a lot more fun and she was identifying what felt like her, but still made her look professional and experienced.
But she had some fun with it too. She likes a preppier style. So she would have these bold pink pantsuits that we found for her and fun, vibrant colors.
And you just saw her energy come alive. And so that's really why I do this. Now, that's amazing because she's already, like she was a partner and had children.
I'm like, stop. Yes. Well, and there's so many of us.
And, you know, same. I mean, I think that as women, we're so used to being high achievers, especially those of us who are excelling at law. We have a family, but we don't necessarily have someone helping us and we don't have someone cheering us on.
And that's a lot of the kind of relationship. A lot of times I have with my clients is to bolster them up because they just style is a skill that can be learned. And it's something that I can teach you.
It's something that I can do. And the reason I'm so passionate about this is that style, in my opinion, is one of the quickest ways to establish authority and confidence. You can go to therapy for a year or you can have a really good wardrobe that you love.
You choose. I'd rather take a couple of months to a great wardrobe and really feel good about myself. And that's just a really underutilized tool that I think is so powerful.
Well, you've been pretty much reiterating this, but just let's, you know, let's, I'm like, you know, let's just one last thing here for the people listening today who feel stuck or uninspired in their wardrobe. What's one small shift that they could make to start feeling more powerful just right away? I would say stop saving your good clothes for special occasions. It's almost like when people say, use your fine china.
Don't wait for the one time a year to use it. Enjoy what you're wearing now. You don't have to have a court meeting or a client meeting to wear one of your powerhouse looks.
If it makes you feel like a powerhouse, wear it now and enjoy it and see how your life starts to change. Thank you so much, Estelle. Thank you.
Absolutely. And thanks for listening to today's episode of Style by Estelle. If you're a woman in law, ready to stop lending in and start owning your confidence, visit estellewinsett.com. That is E-S-T-E-L-L-E-W-I-N-S-E-T-T.com to learn more.
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