Amy Schumer may be known for the confidence she portrays on stage, but her relationship with fashion and getting dressed consistently left her vulnerable and intimidated—until a styling session with stylist Leesa Evans changed everything. The duo were so moved by Amy’s life-changing experience that they launched STYLEFUND, an organization aimed at improving the process of getting dressed for women and guiding them to find their own individual silhouettes to create true confidence.
Below, they share their story:
The Window: Thanks for taking the time to time to talk on a Saturday.
Leesa Evans: This is perfect. We had a fitting today so we’re actually together.
The Window: Let’s start with how you guys met.
Amy Schumer: So I’ve been in some form of show biz for a long time—wait don’t write that word! I’ll send you an Edible Arrangement if you don’t write show biz. Anyway, I had various fittings for different things for many, many years before meeting Leesa. They were always painful, and I mean physically because of tight materials and bad fits, which was bad because I just want to be swimming in cashmere and feathers all the time…
LE: She said to me today that she only wants to wear things that feel like a cloud.
AS: Exactly. And fittings were painful emotionally too. When I walked into that first meeting with you, Leesa, I’m curious as to what you thought my vibe was.
LE: I came to meet you before we ever had a fitting, and I could tell you felt like things would never get better than they were. I never said anything that day—no song and dance about how I was going to make you love clothes. Instead, I just listened.
AS: If I had the option to be put under, like, dental surgery instead of a fitting, I would have taken it. I told Leesa about my style, which at that point was basically jeans and V-necks on stage, and felt like she was cool. Then, we had our first fitting, and it was really emotional. I had never, ever known how to dress for my body—and I don’t want to say “body type,” because it’s not about five specific types or anything…
LE: It’s about proportions. We all have out own individual shapes that make our own silhouette that gives us confidence. Two people the same height and weight might not wear the same clothes. It’s all about the psychology of what makes each of us feel good. That’s where I began with that first fitting. What I wanted to accomplish that day was to show her how great it could be. I wanted to change her mindset about the experience she could have. But I didn’t want to oversell it. She had to feel it authentically for herself as she was looking and feeling so good—and that’s exactly what happened.
AS: My whole life, I had suspected that I was very gorgeous, and then my suspicion was correct! I was ready to feel ashamed and awful, but then I tried on these clothes and as the afternoon went on, I felt and looked great. It was shocking!
The Window: What changed the most that day?
AS: I’d never had anything tailored in my life. I thought if something rode up in the crotch, I’d just pull it down all the time. It didn’t occur to me. Tailoring doesn’t have to be crazy-expensive either—it can be as simple as taking something in an inch at the waist. Leesa gave me the tools without pushing it down my throat. There are ways to dress for all of our different bodies, and we can accentuate the areas we feel confident about. These tools changed my entire feelings about both clothing and about myself. I’ve always been a positive person, but I’d be in a fitting room under those lights and I’d have a shame attack. My life was changed after that fitting with Leesa. I’m the type of person that, when I find something really cool that I love, I want to tell every person about it. It started with me telling my best girlfriends about proportions, and then I was telling the men in my life too.
LE: It’s such a universal thing, which is something that Amy and I figured out through this whole process. All the billionaire clients I have and all the people we work with at STYLEFUND events with Goodwill and everyone in between—regardless of your age, size, or economic level, we all struggle with how we can feel our best.
AS: When Leesa was first styling me, it was for a movie role so she was dressing me for a character, but it was very close to home. It was someone who thinks she’s overconfident but has major self-esteem problems and is a little off-the-mark and trying too hard.
LE: That played into the vulnerability that we all have. I noticed right away with you that you started standing a little taller; it was like your posture changed. There was a lightness—a state of wellbeing.
AS: It really is something that connects all of us. The first time I ever met Hillary Clinton, it was at the Glamour Women of the Year Awards. One of my jokes had been that in L.A., my arms register as legs, and she mentioned to me afterward that she related to that joke. Someone in her position can feel the exact same way as a single mother returning to the work force—we all have these insecurities. Such a big part of my standup and my work is about wanting to make women feel connected, because we are. I wanted Leesa to transform my best friends and change their self image, and then I was like, wait why can’t we share this with everyone?
LE: It’s about us as individuals connecting with what makes us feel good and how can getting dressed every day be empowering and give us confidence.
AS: Versus the trauma! It can be so traumatic, and it always had been for me. When Leesa had the idea for STYLEFUND, I immediately was like, Yes! It’s so close to our hearts. Our first event was really moving and meaningful, and we knew we wanted to reach as many people as possible.
LE: Anyone at any stage in their life—maybe someone coming out of school or having been out of the work force because they were in prison or the military or being a stay at home mother—no matter what the transition is, it’s an opportunity to figure out what it is that makes you feel good in these moments in life. We grow up and change during these transitions.
AS: In fact, we just had a fitting, and we realized that my style had changed a bit—become a bit more sophisticated. I mean, it doesn’t happen overnight—I’m not going from Teresa from Real Housewives to Ariana Huffington, but it’s an evolution. And Leesa holds my hand and walks me through it.
LE: We are psychological dressers. That’s the reason why one day a certain outfit makes you feel great and the next day you hate it. We need to create this uniform in a variety of different pieces and looks, so that we have what we need. For example, Amy looks great in a skinny pant and in a pencil skirt, so if she has both she can choose one based on her mood that day. If we can each find those pieces that make up our shape that give us a sense of ease and confidence, then we won’t be so intimidated by clothing. Then, we can go out and do the things we want and need to do.
LE: Amy starts every STYLEFUND event by connecting through comedy makes everyone feel comfortable. She’ll tell stories that are equally hilarious and vulnerable.
AS: I tell some truthful jokes to make us all feel connected. People know me and are familiar with my work and probably think, she’s a comedian and actress, she has money, but we let people know that it’s not about the money. We say what they know they’re thinking. We’ve all had that experience where you go shopping and suddenly you’re like, I don’t know who I am! It turns into this whole bigger thing! Thrift stores and less expensive retail stores have pieces that can make you feel great. These basic pieces you can mix and match is what we’re helping these women understand and find.
LE: I explain the practical application of this process—how to find your shape, how to build a daily uniform. From that point, we get into the styling with a team of stylists and take questions. We bring in people for hair and makeup.
AS: It’s such an emotional, positive, and beautiful experience. People have major transformations. Everybody cries.
LE: Suddenly, it’s like the very simple version of how much clothing and putting yourself together can change your life on daily basis. It dawns on people, just like it did on Amy that first time we worked together. We get so many grateful emails, letters, and phone calls about people saying that they feel like themselves for the first time.
AS: The change in how they see themselves affects how people’s family sees them, how their employers see them. It’s amazing see these women leave their excuses behind and get down to the reason why it worked instead of the reason that it didn’t.
LE: I hope we all get to the place where clothing, while 100% necessary, becomes so effortless it can fall away from the forefront of our mind. Then, we can feel good and our actions are speaking louder than the clothing that we’re wearing.
AS: The more confident I’ve become, I’ve gotten attention of people telling me I look great or asking me where to get something. I think it’s less about the things I’m wearing and more about how I feel shining through. On that note, I have to go get ready for a show!
LE: Thank you so much. It’s so amazing that Barneys understands our mission. We’re so happy about this partnership!
The Window: We are too! Thank you, Amy and Leesa. Good luck tonight, Amy!
Since we too believe that confidence and feeling good in what you wear can manifest limitless possibilities, we partnered with STYLEFUND this holiday season for our #PeaceLoveJoyProject. Click through to learn how you can participate.