Meet the Stylist Changing Amy Schumer’s Life—She Might Change Yours, Too

You might not know Leesa Evans’s name, but you definitely know her work. Producer Judd Apatow’s go-to costume designer, she’s the sartorial eye behind movies like Bridesmaids, The Five-Year Engagement, and Forgetting Sarah Marshall. Most recently, she collaborated with the director yet again for Trainwreck where she was introduced to star and writer Amy Schumer. The pair hit it off, and now Evans is styling America’s new sweetheart in real life.

You might have noticed that the comedienne’s traded her mini skirts for tailored sheaths, looking more polished than ever before while darting from one late night show to another. And she’s got Evans to thank for that. The stylist has helped Schumer find pieces that not only fit her larger-than-life personality, but make her feel like her best self. In fact, Evans’s personal career philosophy is more than clothes-deep. Below, she tells Yahoo Style what it’s like to dress Schumer and answers the age old question: what’s the perfect airport outfit?

Yahoo Style: How did you get hooked up with Amy? Obviously you worked on the movie, but how did you guys start working together outside of the film?

Leesa Evans: I’ve done a lot of movies with Judd Apatow and Judd had introduced Amy and I before we started getting going on Trainwreck. We just found that we had a really similar philosophy; we just immediately liked each other and we were excited to work together on the film. We kind of thought throughout the process of the film that if it went really well we would ultimately start working together, which we did. We had a great experience all around and found that, not only did Amy start to fall in love with fashion, figuring out what made her feel good and what pieces really made her feel confident for the movie, but also that sort of parlayed into what made her feel so great personally, as well.

YS: Absolutely, you can definitely see that if you look through her red carpet photos and all the recent images that she’s sort of gone from much more relaxed and loose-fitting pieces to more polished dresses. Did you help her to streamline that?

LE: Yeah I think that she started figuring out that the more simplistic style was really something that works for her. She’s sort of an uncomplicated person in a lot of ways, so she loves something that’s effortless. The more streamlined pieces just started to feel really effortless, they were easy for her to wear while walking the red carpet! It just started to become a pretty easy thing that certain things are just simple to throw on and it just makes your life better: Less chaos and complications.

Schumer in a pink Narciso Rodriguez dress at the Apple Store in Soho, New York. Photo: Getty Images

YS: She also acts and talks with her whole body. Does that come into mind when you’re helping her pick stuff?

LE: Absolutely, because I think that, when you’re in a fitting with someone—and I think that this is true about everyone, not just about Amy—but when you’re in a fitting with someone, you can tell when they feel good, there’s a certain posture that happens, and all of a sudden someone stands taller and smiles more, and you can tell they feel good! And I think that that is something that we have picked up on in fittings. We’ll be like this is a definite ‘yes.’ If we’re 100% on something then it’s a yes, if it’s anything less than that, we just let it go and move onto the next thing.

YS: Are there any particular designers that you guys are loving right now?

LE: In terms of designers, she loves a variety of them, and it’s really more about how a piece makes her feel than who specifically designed it. With that said, she’s loved everything from Valentino to Narciso Rodriguez to Zac Posen to Stella McCartney. And she also loves things from H&M and Forever21 and vintage stores — she’s really open minded with it, and is really having fun with fashion.

Amy Schumer at the airport in Australia wearing a red poncho. Yes, that’s Bill Hader behind her. Photo: AKM-GSi

YS: There’s this recent photo that I saw, she was in the airport in Australia wearing this cape and a fedora and her airport style is so perfect. Did you help with that, or did she just immediately learn how to dress like Gigi Hadid sashaying through the airport?

LE: (Laughs) You know what, the truth of the matter is that because the kind of styling I do is more lifestyle, and it’s not just red carpet-related, I really set my clients up with everything they might need in their closet to feel good from the gym to the airport to the red carpet and everything in between, because I think it’s so important in life to step out in things that make you feel great. It’s like there’s something great about a poncho for traveling, because it’s like wearing a blanket! It couldn’t be better.

YS: Yeah she looks so comfortable. It’s a long flight! I’m surprised she wasn’t wearing sweatpants!

LE: You know in this day and age, there are just people photographing you at all times; it’s kinda nice to feel your best when they’re like, ‘Hey, let me take a picture of you!’ I don’t know, but that’s my guess.

YS: It must be so tough to always have to be “on.”

LE: Yeah and you want to be authentic! You don’t want to look like you’re posing at all times, and it’s also very sweet that people recognize her and want to know about what she’s doing and I think she wants to hopefully set a tone for a lot of people who are like, ‘What do I wear in the airport? Oh, a poncho when I’m going to cold weather… it’s like wearing a blanket! That’s perfect.’

YS: Absolutely. And she has such a positive message, you know it’s great because fashion can actually have a powerful message as well, and she seems to be sending that.

LE: I think one of the things that Amy and I connect over most is that we both agree that fashion in its ultimate runway form is art, and then from that point, how does it work in your real life, and it’s really set up to be the first thing that people recognize in your individuality, in your confidence, in your person. So how do you do that with it being very real and comfortable, so that you can walk down the street and enjoy things other than pulling and tugging at what you’re wearing? That’s just the worst, isn’t it? One of the things that came out of doing the film together—it was really our first opportunity to spend a lot of time together—was that she felt that suddenly getting dressed was easy, and that it wasn’t so intimidating. It wasn’t hard and she felt good and it just made her life better — and just hearing her say that, I couldn’t have been happier. It really made me feel so good to know that I would ever influence somebody’s life in that way, and from that point we’ve really both agreed that that’s how it should always be. That’s the ultimate goal.

YS: Absolutely. That’s what you’d want out of your job, right?

LE: Yeah absolutely! Couldn’t be better.

Schumer on the Staten Island ferry doing an epic walk of shame. Photo: trainwreckmovie.tumblr.com

YS: Speaking of your job, I saw Trainwreck a few weeks ago, and oh my god it’s amazing. So there are a few specific outfits that I wanted to ask you about. The first one is the gold skirt and the red top…

LE: It was so funny because while we were doing the film, there was definitely a lot of conversation about how this first outfit needs to explain that this girl is a trainwreck, but what does that? And you still want to love this girl, she can’t have gotten this completely wrong, because you might not fall in love with her. So there really was a lot of playing with it and at the end of the day we just decided like, it was one of those nights where she really made the effort, and got dressed up, and was looking to have a great time, and that parlayed into maybe going slightly overboard and winding up in Staten Island, and then just the whole idea of her having to walk down the hill to get to the ferry in those high heels, and then when she’s on the ferry and has her Titanic moment.

Amy, with co-star Vanessa Bayer who plays her co-worker, wearing a slip top with a blazer. Photo: trainwreckmovie.tumblr.com

YS: How did you figure out her business-casual style?

LE: We wanted to say that maybe this girl goes out on a lot of school nights —maybe she wakes up a little late for work and needs to throw it together and still get to work on time. [In the movie], Tilda Swinton’s character has her up for a promotion, and she believes in her, so this girl must have it together to the point in which she’s potentially going to be promoted. So it’s like she has the pieces that she needs to be stylish and professional and practical, but she pushes it a little too far and only has 10 or 15 minutes to get dressed or she’s gonna be late. So we tried to create this thing that effortlessly it came together, but it just wasn’t planned enough to be perfect. And I think that that imperfection became really endearing and very charming.

Tilda Swinton, Amy’s boss in the movie, plays a magazine editor at a men’s magazine. Photo: Everett Collection 

YS: Absolutely. Especially next to Tilda Swinton’s character, who is impeccably dressed. I’ve worked with those magazine editors before and she plays them to a t — and her outfits are just so perfect.

LE: Thank you. I loved working with Tilda so much, and we had so many funny conversations about editors, and got inspired by the women who do it so well, and we wanted it to say New York City and show the full strength of it. But she wears these little Peter Pan collars, which is sort of this coquettish little girl thing that kind of plays into it too, which was so fun. I mean Tilda’s so incredible, her hair and makeup was perfect with the outfits and her accent was incredible, I mean she just did so well.

Schumer in Stella McCartney carrying a Claire Vivier clutch with Judd Apatow and co-star Bill Hader. Photo: Everett Collection 

YS: I also love the scene where she’s at that luncheon and it’s all about the fashion in that one scene. So how did you go about that picking that one specific dress? Because the whole scene revolves around her dressing in that specific way.

LE: I wanted to show the contrast between the grownups and the non-grownups, and Amy’s still at that transition point that she wants to be grownup, and she knows she needs to dress up, but she’s not quite there yet. So it’s like this moment where you’re rooting for her, you’re like, you can do this, this is an amazing opportunity, this guy is fantastic for you, this budding, beautiful relationship, and the minute we tried on that Stella McCartney dress, we knew immediately that it was perfect for that event, because it was so sleek, and so sexy at the same time, and yet sophisticated at the same time. It was like a complicated moment in her life, and it showed all of that, yet it was incredibly attractive. You wanted her to get it right.

YS: Absolutely. So you’ve worked with Judd a lot before — do you collaborate when it comes to fashion?

LE: You know, Judd is so great to work with because we’ve worked together so many times, and he will flat out say that fashion’s not his expertise, but he has such great taste in general: Great taste in casting, great taste in how the script comes together, production design, and costume design. He sees the big picture so well, so it’s fun to collaborate with him because he’s so open to what you’re going to bring to the table and really expects you to bring something that’s well thought-out. Like you have to have a reason why, that’s not fully expressed in the script, that this would help build the character up and show who the character is. That’s kind of amazing because then you can really talk about why this dress is great, aside from just the obvious of it’s a great dress that looks good on Amy. It’s more than that, because it’s a really important scene in the movie where she’s at a crossroads, you know?

YS: You do this in your other work as well with Judd, like Bridesmaids, where you’ve definitely been able to speak for these women through their clothes in the same way that he portrays these characters.

LE: Well thank you. I think one of the things I’ve always wanted to accomplish is that characters are people that inspire you in some way. They help you be better, smarter, stronger. And whether it’s a female or a male character, I think the clothes help you understand who the person is. I mean I think we all know a girl who was wearing skirts that are a little too short, or a guy who, you just want him to loosen his tie a little, and it was like a metaphor for loosening up in life. And there are subtle things that I think ultimately help you feel connected to the character and as a result it affects you, hopefully, and you feel like, I could be that guy, I wanna be like that! Or, I could get that job, or I could leave my job… you know, all the little things like that, because these characters are going through the same things we’re going through.

More from Yahoo Style:
Amy Schumer Gets Kinky With C-3PO & R2-D2
Fashion at the “Trainwreck” Premiere: A Canadian Tuxedo, Menorah Necklace & LBDs
Why Isn’t Amy Schumer’s Name on the ‘Trainwreck’ Poster?