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On why lesbians dress like men

If lesbians love women so much, then why do they dress like men? Perhaps you’ve overheard someone saying this, or someone has asked you a question like it. Perhaps you yourself have commented, in passing, that lesbians dress like men. Should you be on the receiving end of this inquiry, you might answer by asking why, if heterosexual women love men so much, they aren’t sporting more tailored suits. (This being a flattering assessment of typical male dress.) Conversely you might ask why, if heterosexual men love women so much, more of them aren’t rocking Spanx, and heels.

In Annie Hall, Diane Keaton dons her classic wardrobe of tweed pants, tweed jackets, and white dress shirts. Ellen Degeneres’ style has transformed from tucked-in t-shirts and baggy pants (how lesbians dress, right?) to spiffy tennis shoes and perfectly tailored suits. I’m also pretty sure the Olympic-swimmer-turned-artist-turned-model Casey Legler is gay, yet she models menswear like a natural. Wait, so, the thinking is that we are, or aren’t, dressing like whoever we are having sex with? I can’t keep it straight.

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There’s also Chelsea Handler, who is literally dressed by a lesbian stylist. What does that make her? And there’s her recurring, flamboyant guest-host, Ross Mathews, whose aesthetic might actually provide a context wherein the notion of a person dressing like what they are sexually attracted to gains some traction. But then what about Chelsea Handler’s assistant, Chuy, the tiny Mexican with a permanently broken foot who dons a strict uniform of baggy jeans, Kangol caps, and argyle sweater vests: is he a lesbian? 

Dispensing with the impulse to deconstruct the essential difference between sex and gender or overlay this analysis with the added dimension of sexuality, I’m looking back at some lesbians I’ve known. 

My very first girlfriend was an older, athletic type. She wore lots of sporty pants and sporty tank tops at a time when I wore tattered grey corduroys I’d cut the ankles off of, with a CBGBs t-shirt and red bowling shoes. She had different outfits: for work, for the gym, for the bar. She had long, curly hair, and sometimes wore makeup. I wore the same thing more or less every day, and my hair was shorn into a faux-hawk. On our first date she bleached it for me.

In university I dated a woman who wore only dresses and heels. At the time I worked for a lawyer, and was mostly clad in collared shirts, expensive wristwatches, and charcoal pants. I wore tan leather boots my mother gifted me, prefacing that while they weren’t necessarily the kind of thing I might buy for myself, she thought they would suit me perfectly because they looked like a gay man’s boots much more than they resembled women’s footwear. I matched my belts to them. I buffed them. I loved them. At the time, I was getting more frequent haircuts than ever before or since, and my girlfriend never left the house without makeup on despite being one of the most aesthetically beautiful humans I have ever in my life set eyes on.

The woman I dated in graduate school was a dancer: she dressed more or less exclusively in leg warmers, arm warmers, Thai pants, and a sweater tied haphazardly across her chest, along with the odd Spandex piece thrown in for good measure. During our relationship, I wore flannel shirts bought in the menswear section at J. Crew that I shrank down to size by tossing them in the dryer, and various deck shoes. I was striving for a New-England-academic-goes-to-Vermont-for-the-weekend look, and she often joked that her style was modeled after “the village crazy.” This dispensed with the fact that her mismatched frocks were easily worth the price of my entire closet’s worth of shrunken menswear. It really is all about how you wear it. 

Then there’s my best friend, who entered my life shortly after I had given up working as a bicycle courier – tattered cargo pants, layers of stripy t-shirts and stripy sweaters, Asics sneakers, American Apparel socks with stripes at the top, pulled high, and a messenger bag with a strap running diagonally across my chest – and started college. I arrived on campus wearing burgundy Adidas tennis shoes, a pair of distressed Diesel jeans, and a pink dress shirt, the collar popped and the shirt overlay with a yellow sweater vest made of wool. I noticed my best friend walking across the quad, smoking a cigarette. I was about to have one of my own. I walked as quickly as I could without seeming like I was charging toward her, and asked if by any chance, she had a lighter. When she looked up at me, she stopped walking. She stared while rifling absentmindedly through her man purse. Slight variations notwithstanding (at the time, she tended more toward navy blue, dark green, and touches of orange, while I preferred bright pastels) we were wearing the exact same outfit. She lit my cigarette and I said thank you and we said goodbye because both of us were too stunned to speak. We would meet again soon, but we would never have sex.

Marie-Hélène Westgate is the interviews editor for Freerange Nonfiction. She earned a Masters of Fine Arts in Nonfiction Writing from Sarah Lawrence College.

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