45: What To Wear and Why with Estelle Winsett

Andrea Liebross |

www.andrealiebross.com |

Episode 45

Speaker1: [00:00:09] You're listening to the Time to Level Up podcast. I'm your host, business life coach Andrea Libros. I help women in business commit to their own growth personally and professionally. Each week, I'll bring you strategies to help you think clearly gain confidence. Make your time productive. Turn every obstacle into an opportunity. And finally overcome the overwhelm so that you can make money and manage life. Let's create a plan so you have a profitable business, successful career. And best of all. Live with unapologetic ambition. Are you ready to drop the drama and figure out the how in order to reach your goals? You're in the right place. It's time to level up.

[00:00:57] Let's do this.

Speaker2: [00:01:07] Hey, time to level up, listeners, welcome back to the podcast. So today I have with me Estelle wingsuit and she is an attorney, but she's also a style coach. And she and her family live in Memphis and virtually she connects with women across the U.S. to help them figure out what message they want to send through the clothes they are putting on their body. And she helps them figure out what are their style preferences? Are they a dress person? Are they a pants person? Then she helps them determine what their body shape is and off they go. Doing some online shopping, I used to be in the business of clothing and I used to help women style themselves, and I actually, when I think back, I loved that part of that job. There are parts I didn't like, but I did love the helping women create their style part, so I thought this was amazing guest to have on because so many of you, whether you're working from home, going into an office, whatever it is, even on weekends, you stand in your closet and wonder, What should I wear? I have nothing. So today, Estelle is going to give us some tips on how to think about what's in your closet, how to add to it, and then how to go out into the world. So sit back, buckle up and listen in to my conversation with Estelle.

Speaker3: [00:02:38] Hey, time to level up, listeners. Welcome back to the podcast and I am excited for today's guest because what she does, or one of the many things she does, is something that I kind of sort of used to do in a different way and slightly different way. But she and I connected online and I asked her to come today, talk to us about style and what to wear, and why do you wear it in all things clothes and closets? So welcome Estelle wins it.

Speaker4: [00:03:10] Thank you. I'm excited to be here. So tell us, just

Speaker3: [00:03:13] Tell us a little bit about you before we get started so they they know where you're coming from. I'm looking at her on Zoom right now, and she's got a beautiful office park setting behind her and big glass windows, so she is not shopping right now.

Speaker4: [00:03:25] I am not. Yes. So I am an attorney. I like to say I'm a recovering attorney. So I practiced for about seven years in litigation and I got to the point where it was a little bit to. I had a hard time separating work from home, so I took a nontraditional route with my law degree and I was a legal recruiter and then I was in career services. And now my day job is director, professional development at a law firm. But my passion and my side hustle is in personal style, and in particular, I love to help women who are in executive roles or entrepreneurs or attorneys learn how to show up powerfully and how they dress. So that's just something that I have always love, style and kind of like you. I know you were at work for a designer. I did work for Kabhie for several years and saw the transformative effect when people finally saw what they look like with clothes that fit their body and made them feel powerful. And so that's really how I got into the whole personal stylist business.

Speaker3: [00:04:32] It's fun, isn't it? Yeah. So why do you think it matters? Does it matter what we wear? What do you think?

Speaker4: [00:04:39] Yes, because what we wear sends a message to ourselves first and foremost. And if you think about it, how many times you pass a mirror, you pass a window where you see your reflection. If you don't feel confident what you're wearing, you send these messages to yourself. And often they're unspoken and probably unconscious, but it translates into your energy and how you show up. And so when you do wear something that you feel empowered in, then you can go and slay your day and you're not worrying about what you're wearing. And if you made a wrong decision and if the skirts actually a little bit too small and you're tugging on it and all those things we do as women, it's junk that clutters your head that if you didn't have to worry about it, then you would be on your game and it's a mental load when you don't feel good with what you have on.

Speaker3: [00:05:33] Yeah. So I think we send ourselves messages like, I call it head trash, but then we carry it around, like we carry around all of that. What if I don't know, is this right? I wish I was 10 pounds lighter. We carry that because it's because the skirt is too tight. We carry that around all day, and it kind of does affect us. I will say this morning, to be honest, I'll give you an honest example. So I put this sweater on because it's kind of comfy. And then I was going to put jeans on, and then I said to myself, Now I'm going to put some real pants on today because I felt like this. I was at a meeting. This morning and together, it all looked way better than Nance versus the jeans. So there you

Speaker4: [00:06:10] Go. It's so small tweaks right in your mind, you think, Oh, I don't have time for that. It's going to take way too much time, but it's like a little tweak makes such a big difference.

Speaker3: [00:06:21] You're so right. You're so right. So what do you think your closet says about you?

Speaker4: [00:06:25] I think your closet says a lot about how you think of yourself. I think if you put yourself first, then you're going to have clothes that fit your body as opposed to those aspirational garments that,

Speaker3: [00:06:42] Oh, I like that aspirational garment that is so good. Can I write that down? Asprey Yes.

Speaker4: [00:06:47] Yes, yes. Yes. The other thing too is and I'm just really passionate about this because as a woman, my weight has fluctuated a lot too. And when I've had those garments in my closet that are like, Well, when I lose 10 pounds, they'll fit. And I think in my mind, well, having those hanging in my closet is going to inspire me to get on the plane and go running. And the reality is it ends up making me feel bad about myself because I don't fit. So, yes, you know, I think that what's in your closet is kind of a reflection about how you feel about yourself. If you feel like you're worthy and deserving of clothes that fit your body now and you can still work on trying to lose 10 pounds if that's your goal. But you're not going to punish yourself by saying, I'm not allowing myself to go or I hear this all the time. I'm not going to invest in myself until I've lost the weight. Well, that's just it.

Speaker3: [00:07:39] Is that that phrase, though? You know, and think about this actually, now that you said that, we say that about a lot of things, I'm not going to invest in myself. Whatever that might be, it might be clothing. It might be coaching. It might be like whatever. That is so interesting. Why are we doing that? That's not helpful at all. It's not useful, really.

Speaker4: [00:07:59] It's not. You hold out on yourself and you don't realize the toll it takes on you.

Speaker3: [00:08:06] Yeah. It wears you down. So what happens, what light bulb usually goes off when someone says, OK, I actually am going to care about this and then they freak out, I'm going to guess the next thing is, Well, where do I start? What do you think they're thinking when they decide that they're going to care? And then what happens?

Speaker4: [00:08:26] Well, I think there are a few different things that can happen. I think one thing that can happen is, Oh, no, I don't want people to think that I am better than them or who does she think she is dressing that way? There's this like imposter syndrome thing that comes up that if I change how I appear, people are going to ask me a lot of questions and think negatively of me. And somehow I think another thing that happens is if you've always struggled with style and you decide you want to do something about it, if you don't have a guide and you go back to doing what you've always done, then it's frustrating and you're going to want to give up. Because if you've not been successful in the past, if you don't have some new resource or doing something differently than everything you've done, then it's going to be frustrating again and you're going to waste a lot of time and energy and give up. So I think those are kind of two of the common things that I hear women say when they're trying to finally do something about it.

Speaker3: [00:09:22] Where do you start? Should you start in your closet? Should you start at the mall? Should you start online? What do you think?

Speaker4: [00:09:29] Yeah, well, it's interesting. When I work with clients, the place that I start is in crafting their new elevated style. So before you go shopping, before you clean out your closet, I think it's important to think about what's the message you want to send and how you show up. And that involves the messaging piece. Do you want to feel more confident? Do you want to feel relatable? Like sometimes you know, when I'm working with clients, they may be a plaintiff's lawyer into their meeting with maybe more indigent clients, but they want people to feel comfortable with them. So they don't want to come in with this power suit and intimidate people, so they may want to send the message of being relatable. So I think when I work with someone, I just think about your next level image and the message you want to send. And then I think it's important to try to figure out what is your style esthetic because there's a variety of different ways that people have a natural preference for. So it can be maybe you like more of a classic look, or maybe you like to have a little fun with lines and asymmetry or little details. And so maybe you're like a little edgy? Or look, there's a there's a range of looks that are still professional, but that allow you to show your personality. So I think when you're figuring out like, I like to call it your authentic style blueprint, I know the message you want to send your style preferences. And then that third element is really understanding your body shape and how to dress it. Because if you buy things that don't fit your body, then you're not going to feel confident. So those are kind of the three things I think I think about, and I work with clients on doing. And then the next step is to find a wardrobe that's in alignment with that blueprint so that it fits your body size, the message you want to send and something that you feel good and competent in.

Speaker3: [00:11:20] I like that. I like the three element, the message message. That's really important. Yeah, that is really important. So, so let's talk about like the person that is maybe the work from home person. I think sometimes they get stuck in what they're wearing, but then all of a sudden they worry because they're on Zoom. Or I don't. Tell me about that work from home person. Like what's going on in their brain usually?

Speaker4: [00:11:45] Yeah. Well, I think those of us who have worked from home for this long period of time, and I know several still are. Thankfully, I'm back in the office and I really appreciate being back in the office. But I think one of the first things people often think is if I wear this outfit one more time, I'm going to scream, Yes, yeah, I've been wearing it for a year and a half now. So, right, right. I think that's that's a common thought. Stores are not all open. So if you're not comfortable with online shopping, then you probably haven't been out in the stores. And so there may be some trepidation about not knowing how to shop online. I know that several people feel super overwhelmed if they go online to Nordstrom or something like that, because there's so many options they don't know how to pair it down.

Speaker3: [00:12:32] So how do you pare it down like a Nordstrom? I mean, do you have any good tips on that one online shopping?

Speaker4: [00:12:38] Yes. So first and foremost, before you do any online shopping, create an intentional shopping list. I liken it to if you go shopping online without an additional list, it's almost like going to the grocery store hungry. You're going to buy things that you don't really need or like, but maybe they're on sale and then that's another one that's going to hang in the closet with the tags on for years. So first and foremost, have your list and OK, the way you want to come up with your list is after you've done the closet cleanse. And you've gotten rid of anything that doesn't fit your body or your new elevated style, categorize everything, put them in blazers, tops, skirts, bottoms and you'll see where the holes are. If you've got 15 blazers and one pair of pants, you're going to need some more bottoms.

Speaker3: [00:13:24] So, right, right?

Speaker4: [00:13:26] Yeah. You assess basically assess the keepers that you have in your closet and then create a shopping list to fill in the gaps. And so when you go shopping, just start with a narrowing of the search if you know you need a skirt. Then you narrow it by color, category and size, and that's going to limit your options. And you could even do it based on low to high or high or low over your shopping so that you're staying within a budget, set a budget for yourself. So I think that's the easiest way to do it and just go from there. And sometimes, if you're in between sizes, you might want to order two sizes. The most accurate way to guess what size you're in is to literally do your measurements of your bust your waist in your hips and then look at the size charts online. That's what I do with my clients, and I know that can be tedious, but it helps because there unfortunately is no universal sizing standard.

Speaker3: [00:14:16] No, there is not. I had to look up yesterday. What a what is a size three mean? Yes. Yeah. Yeah, exactly. So, OK. So when people start to elevate their style? Ok, what do you see happen? What happens to them or what are they thinking or feeling?

Speaker4: [00:14:34] What I love is to get the giddy text messages and emails of all the compliments they're getting because it's the ripple effect. You feel good. Then people can see there's a different energy about you. They like what you're wearing, so you get compliments. And then it just it's almost like a compounding effect of feeling good, looking good, feeling good. That then allows them to go out and have more fun in their life.

Speaker3: [00:14:57] More fun. Who doesn't want more fun, right?

Speaker4: [00:14:59] And then that affects how they show up everywhere, you know, in their relationships with their spouse. You know, sometimes you'll have your friends that they don't know what's different. It's almost like when you get a new haircut. They know something is slightly elevated or different, but they just feel that you're happier. And you also realize you probably didn't realize the kind of mental load it had on you, not knowing what to wear and standing in front of your closet 20 minutes every morning and how that impacted how you start your day. I find that people who maybe weren't that excited about style but knew it was important then when they actually have fun with it, it almost surprises them.

Speaker3: [00:15:32] So because it can be stressful, just thinking about it, right? Like that mental load, like you said, Yeah, so do we have to have like separate wardrobes, work and play and weekend? Or do you think they all can meld together? I think. I hear people say all I have are either Lululemon for dresses like there's nothing in between.

Speaker4: [00:15:58] Yeah, I definitely think they can marry and play well together. I do think when I'm advising people, most of my clients are looking to me for a professional wardrobe help. And one of the things that I always tell them is put all of your workwear in the front of your closet because if you're trying to wade through jeans or a gown or something and you can't get to your clothes, it's very frustrating. And so I think I recommend putting that first and foremost, whatever that regular lifestyle style is for you, put that the front, the closet. But in terms of weakened, where I love a nice blazer and a good pair of jeans and heels for date night, I think if you expand your mind of what you think of when you think of casual wear and see, well, what do I have? And really, it's about it's about playing. I love to play in my closet. I know a lot of people don't like to do that. But when you do and you find something you like, take a selfie, put it in an album. And then when you're having, I don't know what to wear a day, you can look at your phone and find something that you put together. That was fun.

Speaker3: [00:16:57] Maybe we should all take advice from 17 year old girls because this is what my daughter does. Yes. I mean, for real. She plays in her closet. She creates outfits. She gets all excited about them. She takes selfies. It's this is kind of interesting. And she just had to fill out a form for senior pictures and describing what her style was. And she came out of the room. Mom, what should I write for this? I said, I don't know. What should you write? Come up with some words. So she actually I'm like, I forget even what her words were, but you nailed it. That is exactly what you are. So but it's funny because they take all these selfies and we don't I don't think, you know, 40 and 50 year olds are taking as many selfies, right? What do I know? What do I? So do you work with people in person or virtually? Or how do you do things?

Speaker4: [00:17:42] Yeah, really. All of my clients are virtual, and it was that way before COVID. And for me, the reason I do that is, well, first of all, Memphis is not necessarily a mecca of style.

Speaker3: [00:17:51] So you never know. I mean, I don't know what is the style of Memphis if we had to go for it, right? Who knows?

Speaker4: [00:17:57] Who knows. I think the people that, well, there are certain boutiques that I love, but I think that the people that are probably the most stylish shop elsewhere. Yes. Yes. Yes. You know, so yes, all of my clients are virtual. I do all of my shopping online and really through Zoom. And going back and forth with emails. And then I record videos for clients. So when I'm sending them recommendations, I have a video explaining why I chose the different pieces and why it works for their body types, so try to educate them. It's really kind of seamless, and I have a platform where I put outfits together and they get their own online closet, which has an app on the phone and so really had lots of women virtually. And it's it's worked out great.

Speaker3: [00:18:40] It's worked out great. Imagine that even before COVID. Yes, even before it. Definitely. Yeah. So if someone wanted to work with you, what's the best first step?

Speaker4: [00:18:51] Yeah. If someone wanted to work with me, they could either book a call with me or they could go to join my free Facebook group. That's where I spend most of my time, and that's powerhouse style. So it's just I have a shortened link that's battle for powerhouse style. So it's all I want to do that they could join me there. I have an Instagram account and I spend some time there, but most of it's in the Facebook group.

Speaker3: [00:19:15] Tell me because I've been in the Facebook group, so tell everybody what you do in there because I think it's kind of fun.

Speaker4: [00:19:20] Yeah, it's so much fun. So it's a bunch of powerhouse women that, you know, we have a lot of posts. People share what's going on in their life, you know? So it's a lot of bonding with a lot of other women who are in professional settings, and maybe they don't have that outlet to be with other professional women. And every week I do what's called I call level. So I love that your podcast is about leveling up, which is great. That's true. I do different things right now. I'm in the middle of a style coaching series where I have been coaching lab women that have the types of style struggles that I hear the most. So when we did, I know how to look professional during the week, but I don't have any profession where, like you were saying earlier on the weekend, I don't want to be just in Lululemon on the weekend when I did recently was how do you use jewelry to amp up your look? I feel like accessories can baffle people sometimes. Yeah, yeah. So we did a style coaching on that. I did one on all wears black, so I helped.

Speaker3: [00:20:17] Yes, know those people totally.

Speaker4: [00:20:20] And I used to be one no judgment. But it's so much more fun when you can incorporate color and learning what your colors complement your skin tone and things like that. So, yeah, so just provide a lot of style tips. It's fun. It's girl time, and it's just a really cool community. But I love being a part of.

Speaker3: [00:20:39] I love it when you go live and people are in there and everybody recognizes themself in someone else. And I think that's actually some of the best learning when you see yourself in another person and then you recognize, Oh yeah, I'm doing that too. So I like that a lot. So right now, what's your most favorite thing in your closet?

Speaker4: [00:21:01] Ooh, that's a great question. Actually, I haven't gotten it yet. It's on the way, but I'm always thinking about purchases

Speaker3: [00:21:09] The way we shop ahead four seasons. I mean, what do you how do you

Speaker4: [00:21:14] Shop all the time? So yes, I do like to have my seasonal wardrobe together, but there's a brand that I've started liking lately, and I think it's great for professional women and it's called Anna Kate.

Speaker3: [00:21:24] It's like CMT.

Speaker4: [00:21:25] And I have this relationship with the woman who owns a boutique in original Mississippi, which is where my the main office for my day job is and just ordered two dresses from this brand called Anna Kate, and I can't wait to get it. One of them is black and one of them is navy, and they're just good cocktail dresses and they're just, they're feminine, but they're professional. So I'm super excited that's supposed to be arriving, I think today.

Speaker3: [00:21:47] So look at that UPS and FedEx helping us out, helping them feel more empowered. When is it going to get here? We can track it. I know sometimes that tracking is good and sometimes it's not absolutely great. Well, this has been really fun. All of Estelle's contact info that Facebook group link, everything is all going to be in the show notes. And if, if anything, go check out our Facebook group because I think there's a lot of good stuff in there. And I would say from my own personal experience, when I see women caring about what they look like, really good things happen. It's kind of one of those things. Once you start to pay attention to one aspect of your life, other things come along, and even the people that are buying the clothes thinking they're 10 pounds overweight, somehow that's way more helpful to actually lose the weight than to wait around till you lose the weight. Yeah, because the thing isn't

Speaker4: [00:22:41] It better about how you look when you're in clothes that fit your current body?

Speaker3: [00:22:45] Yes. And I think you just show up in a whole different way than if you weren't feeling good about what you were. It's really what you're wearing. You can feel actually, this is interesting about like you can be not liking necessarily, let's say, the weight you're at, but you can like what you're wearing and that will overpower it.

Speaker4: [00:23:03] Yes. And you know, accessories and shoes always fit.

Speaker3: [00:23:07] They do jewelry to jewelry to jewelry, too, so. Well, before we started recording, I said something to a spell that I want to share with you, either I think with with style. We can either not care enough so that it doesn't we say, oh, it doesn't matter or we can care too much to the point we become paralyzed. So finding that middle ground is the key, it's can be tricky. But if you, I think, have a guide and you are making it a kind of a goal even to get your act together, get your closet together, it's possible.

Speaker4: [00:23:44] Absolutely. And one of my favorite tips to give women is if you take an hour out of your sun and look at your calendar and see what's coming up the next week and put together five outfits, you could put them at the front of your closet and your morning will be two minutes. And it seems like it's a lot to take an hour. But the average woman spends 20 minutes staring at her closet in the morning trying to figure out what to wear. So that's.

Speaker3: [00:24:08] And then use where the black pants and the black top.

Speaker4: [00:24:10] And then you still don't wear the same thing you always wear.

Speaker3: [00:24:13] Right, right. Yeah. Yeah, that's a great tip. I like that. Yeah. All right, friends. Until next time, go check out what's in your closet. Do that audit and then create your list and see see where the holes are. I bet you're going to find some some, but you're going to find actually some great things in your closet and then know what you really need to get.

Speaker4: [00:24:33] Definitely, when you clean out your closet, you're going to find those gems that you forgot about and then you just need to figure out what to pair with it. So you wear it, not have it hang in the closet, right?

Speaker3: [00:24:42] Right. And Estelle can help you, so reach out. Thank you so much. This has been great.

Speaker4: [00:24:47] Thanks. It's been a lot of fun.

Speaker2: [00:24:49] I want you to think about what you're wearing right now as you're listening to this now, you might be on a walk or you might be in your car, or you might be even at home on your couch. But what are you wearing right now and how do you feel in it? Do you feel powerful? Do you feel in control and I think you can feel that way, even if you do have Lululemon's on. But when you leave your home or when you are in front of people, what you wear matters. It totally matters. So I hope that you take advantage of Estella's free Facebook group and even connect with her if you need help in this category. And let's be honest, who doesn't? Most of us do. It's always good to get someone else's perspective. Just like in the coaching I do, I say we're stuck in the peanut butter jar and we need someone to read the label. So you might be stuck in your own clothing and you need someone to help you find new labels. So take a peek at the show notes. Find all of Estelle's links, and if you need help actually getting out there into the world and feeling like something is holding you back, but you can't figure out what it is. Feel free to reach out to me and schedule a call and we can figure out what that thing is. Ok, my friends, until next week. Remember, it's always time to up your game to level up. See you next week.

Speaker1: [00:26:19] Thanks for listening to the Time to Level Up podcast with me. Your host Andrea Libros. If you know someone who could benefit from listening to this episode, I encourage you to take a screenshot and share it with them. Ok, now what about you? You've listened to the podcast, and if you now know that you're ready to upgrade your life, upgrade your business, upgrade, you then stop being only a listener and start being a liver living that upgraded life. Head over to my website and schedule a call right there on that call. We'll start changing the way you think and act so that you can have the freedom to achieve the impossible in life and business and have the resources to do it. You deserve an upgrade. Let's do it.