When Will Womenswear Catch Up To The Way Women Actually Dress?

Women have been donning traditional male dress for decades—from Marlene Dietrich starting a pants trend in the '30s to Patti Smith's debonair blazer, tie, and white button-up combo on the cover of Horses in the '70s—but it wasn't until 2013 that a one-stop shop dedicated to menswear-inspired womenswear arrived on the scene. Online retailer Wildfang, the brainchild of Emma McIlroy and Julia Parsley, declared itself "the world's first home for tomboys" and quickly found grateful fans far beyond its brick-and-mortar Portland store. Now, with trendy labels like Hood By Air and Eckhaus Latta continuing to stick their middle fingers up at archaic stereotypes, and LGBQT tailor Bindle & Keep about to hit HBO in a Lena Dunham-produced documentary, it seems gender-progressive style is finally on the verge of going mainstream.

"Many of the people we spoke to in our journey to get here felt like they were being restricted or excluded in some ways," says Wildfang's McIlroy of the previously limited options available to women who don't feel at home in "girly" clothing. "That's a shitty thing, when you can't self-express. No one reaches their full potential when that's the case." For their part, Wildfang offers oversized suit separates and easygoing sweaters for off-duty days, designed for "women who want to break out of social norms and rock stuff from a department that they weren't traditionally allowed to shop in."

To that point, we brought together eight women from different spheres—including fashion, but also music and fine arts—to discuss what it means to dress as a woman today. Below, they talk about how they found their personal style, the judgments they sometimes find themselves up against, and why gendered clothing could one day be a thing of the past.

In order of appearance:

NAR—DJ, Los Angeles
PALOMA ELSESSER—Student and writer, NYC
JULIA PARSLEY—Wildfang co-founder, Portland
CHRISTELLE DE CASTRO—Photographer, NYC
DEJ LOAF—Rapper, Detroit
AVIGAIL COLLINS—Stylist for Lorde and Jessie Ware, London
TAE PAGE—The Brklyn Store founder, NYC
EMMA MCILROY—Wildfang co-founder, Portland

When did you realize you weren't into "girly" clothing?

NAR: For my first birthday party, my sister bought me a Christian Dior dress, and I cried hysterically until they took me out of it. Growing up, my parents would buy me boy clothes because that's what made me happy. Looking androgynous was never a fashion trend for me; it's a part of who I am.

ELSESSER: When I was 14, this boy was like, "Yo, if you show weakness, people will take advantage of that shit." I was like, "Wow." Because I do have a very vulnerable side, and I'm super sensitive, but I don't fuck with being taken advantage of, ever. I think that at a certain level, I reflect that in my outer appearance.

PARSLEY: I can remember being very young and going into stores and getting herded over to the little girls' section and feeling this kind of shame, almost, like, "That's not what I want to wear; that's not me at all." I always gravitated toward the boy's section. It was just functional: I was going to be able to run around; I was going to be able to chase the boys; and it just fit more with the style that I thought was really cool.

What's your personal style now?

ELSESSER: 98 percent of the time I'm wearing sneakers, just for comfort levels. I tried to be a heel girl for a second, and I couldn't. I felt so out of myself—so uncomfortable, physically and mentally.

DE CASTRO: I really don't feel comfortable in anything tight—anything that really accentuates curves—which is why I like to wear sports bras. The best way I can explain it is that androgyny makes me feel pretty. It's how I interpret feeling like a lady.

DEJ LOAF: I never really go into the men's section. People used to vibe, "Where did you get that?" Out of the women's section, over there. It's just how you put it together. What I'm wearing in my new video, it's mostly pimp style. In other words, slacks and loafers. I can't go wrong with that look—I'm DeJ Loaf.

COLLINS: Personally, I can't dress like a boy—I'm very curvy—but if I could, that would probably be my uniform. When I'm styling Lorde and Jessie Ware, it's me dressing them how I wish I could dress myself sometimes. I love the whole white shirt and tuxedo trouser vibe—what's sexier than a woman in a suit? There's something about not showing too much skin that's sexier. Lorde was only 16 when I started working with her, and if you hear her music, you might think you're going to see her in a pretty little lace dress. But she really wanted to wear sports bras with suits. It's her being like, "Actually I'm really powerful and I can wear a suit and own it."

How do you feel about the term "tomboy"?

DEJ LOAF: Back in the day, it wasn't cool. I used to get teased a lot—[getting called] "tomboy, tomboy"—which I really didn't like. I learned to embrace it, though. Girls made fun of it, but the guys they'd date were crushing on me. Now I'm confident, like, "I'm going to wear this, and you'll see. Your boyfriend will be on my Instagram with heart eyes."

PAGE: I'm pretty comfortable with people's terminology for things, because I feel like that's your terminology. Personally, I'd [say that I] dress masculine, traditionally speaking, [but] I think we're making progress accepting the tomboy look. And that's a great thing, because people should dress how they feel.

NAR: People always addressed me as a "tomboy" growing up, but I never felt that term defined me. I had gone through a gender and identity crisis most of my life, and the term that I identify with most is trans.

DE CASTRO: I identify as gender nonconformist. Technically, I'm a transvestite, because I only wear men's clothes; if a dude were only to wear women's clothes, he would be a transvestite. [But] the word "transvestite" is limiting, because it's gendering clothes. Why can't you just wear [something] if that's what you wanna do?

ELSESSER: I've been a tomboy my whole life, [especially] when I was younger and I couldn't figure out the balance. But I'm also very much a girl, so I don't know if people would describe me as a "tomboy" anymore. I just don't dress like a basic girl.

MCILROY: Tomboys are not provocative. They're bold, they're confident, and they're strong. Marlene Dietrich didn't wear a suit because she wanted to make a huge point for feminists around the world; she wore it because she wanted to get into [Venetian] gondolas more easily, and dresses didn't make sense to her.

How do you want people to perceive you, and how do your clothes help you achieve that?

NAR: I want people to see my beauty for who I am, not because of what I wear. Since my face and style are very ambiguous, most people perceive me as a boy at first. I have always covered up the parts of my body that look feminine, specifically my chest. It's very difficult for me to use public restrooms because people stare or tell me I'm in the wrong bathroom. I don't enjoy attention from people looking at my body as an object of sexual desire. I prefer people being intrigued enough by my look to actually get to know me.

PAGE: I want people to see me as somebody who really doesn't care [what they think], first of all, but also as somebody who's just proud of themselves. I think that my clothes show that because if I'm wearing something that I'm comfortable in, then I'm going to rock it. I'm choosing not to conform, and it's not even to make a statement or anything like that—it's because that's who I am. It just happens to be a statement in society's eyes.

ELSESSER: I've never been skinny my whole life, so beyond what I am supposed to think women should dress like, I have an idea of what women are supposed to look like. I'm still dealing with that every day, [but] I feel like a woman in my body—very much so—and have learned that womanhood is not defined by being thin or being sexual or being any of those things. I've gotten responses like "Wow, you're mad confident" because I wear what I like to wear. Even if I'm having a shit day, if I put on my kit that I feel good in, [then] nobody can fuck with me.

How are things changing?

DE CASTRO: At this moment, fashion is finding evolution in new technologies within the activewear space, within the sporty world. Maybe as a reaction to that, more and more women seem to be dressing more comfortable, or utilitarian, rather than sexy. And maybe we receive that as women dressing more like men, or being tomboys, when really they're just wearing sporty shit.

COLLINS: My brand Silver Spoon Attire launched a unisex collection of leather jackets in 2007. It came about because I was always stealing my husband's jackets, and it got to a point where I was buying really masculine ones so he was stealing mine. At the time it was alien—stores just couldn't understand which section they should go in—but now I feel like everyone just kind of wears all their boyfriends' stuff and vice versa.

MCILROY: I don't know if it's going to be occasion-based, or lifestyle-based, but there is going to be a day in the future when mass retail is not merchandised for "men" and "women." [For the record], you won't see Wildfang do hyper-sexualization. We believe that there's another way to show sexy and confident aside from simply showing more flesh.

DEJ LOAF: With life, there's a lot of traditional things that we do, that we were taught from early on: what to dress like, what's cool, and what's not. [But] there's no rules—I go by that all the time. There's no rules, really.

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Additional reporting by Jessica Robertson.