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Beyond ‘boyfriend’: How the tomboy look is going mainstream Add to ...

When I was growing up, I was often mistaken for a boy. I guess you could say I was a tomboy (or what Larry David might call “pre-gay”). I had short hair, wore my older brother’s hand-me-downs and felt a profound sense of disappointment with the girls’ shoe section. Once, when I was six, my mother attempted to put me in a dress for synagogue, but I ultimately emerged, triumphant, in ripped jeans and hightops as we left the house.

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At 33, I’m still mistaken for a boy, albeit a 17-year-old one. My nickname among friends and colleagues is Lil Bro. I often cross the floor to the men’s section to buy my clothes and have to compete with the boys come sale time for size 6-and-a-half designer oxfords. My sartorial role models include Ellen DeGeneres, One Direction and Shiloh Jolie-Pitt. (Have you seen Shiloh’s collection of blazers? To die for.) But boys’ clothes don’t fit the way they did when I had no hips and breasts and it became a constant quest to find masculine clothes that fit my body, my style and my sense of self.

Thankfully, there are more options today than Topman’s XXS collection for women who like a “masculine” cut. In February, Tomboy Tailors, described as a bespoke clothier that caters to “butch/ boi lesbians, female-to-male transgender individuals and people of any identity who like to don tailored men’s wear or tailored women’s wear,” opened in San Francisco. And just last month, the Portland-based tomboy shopping site Wildfang launched, aiming to liberate men’s wear “one bowtie at a time.”

Wildfang and Tomboy Tailors are just the newest among a handful of “genderqueer” clothing lines to pop up in recent years. There’s the Butch Clothing Company in Britain and Saint Harridan, Fourteen, Marimacho, Haute Butch and Androgynous in the United States. And Toronto-born Kiyomi McCloskey (of the band Hunter Valentine) recently told the transgressive-men’swear blog dapperQ that she’s starting a clothing line called Death and Diamonds for people who, like herself, aren’t afraid to play with “a little bit of femininity but are more androgynous.”

Tomboy Tailors’ 48-year-old owner, Zel Anders, a self-described butch lesbian, says the idea for the company grew out of her frustration with trying to buy men’s wear off the rack. Besides overspending on alterations, she was tired of salespeople’s discomfort with selling her men’s clothing. While Anders caters primarily to transmasculine individuals, she wants everyone to feel comfortable at Tomboy Tailors. “I want it to be known as a friendly place, not one that excludes people,” she says by phone from San Francisco.

The brand’s focus will be on shirts, formalwear and made-to-measure suits, which can be cut from more than 350 high-quality fabrics (from herringbone to plaid) and can be purchased\ in-store or online (it ships to Canada). Anders also plans to offer a variety of dapper accessories, including men’s dress shoes in smaller sizes.

So far, Anders says, the response has been positive – in the week before Tomboy Tailors launched, 3,000 people signed up for its newsletter.

How to explain the emergence of boutiques that cater to women who want to wear men’s-style clothing? “There has always been a market, but I just don’t think that society was ready to challenge binary gender expectations,” says Anita Dolce Vita, dapperQ’s managing editor.

Dolce Vita sees these new clothiers as part of an overall renewed interest in men’s wear and says they recognize that “even straight women don’t always feel comfortable running around in pencil skirts and pointy heels. You don’t have to be a lesbian to want to wear a sensible suit.”

Even the mainstream fashion industry is reflecting a shift in thinking about gender: New York-based artist Casey Legler recently became the first woman to be signed exclusively to Ford Models’ male roster, while Saint Laurent Paris cast Dutch model Saskia de Brauw, who has a boyish hairstyle and wears skinny suits, in its spring 2013 men’s-wear campaign. Raf Simons, meanwhile, opened the Dior spring 2013 women’s show with a model in a black tuxedo. And Dries Van Noten’s boy-meets-girl collection at the recent Paris fashion week featured traditionally tailored men’s-wear staples embellished with bright colours and worn with flat shoes.

Among mainstream brands like Old Navy and J.Crew, the “boyfriend” look is, of course, ubiquitous. Popularized by Katie Holmes when she stepped out in Tom Cruise’s jeans nearly five years ago, boyfriend style tends to be oversized and undertailored and, by definition, isn’t meant to look like it was designed expressly for women – think Old Navy’s slouchy fuchsia “boyfriend blazer” or a cashmere J.Crew “boyfriend sweater” constructed to hang long and bearing seams that droop over the shoulder.

Nevertheless, I was happy when boyfriend style did emerge. Finally, I could find blazers like Shiloh’s that fit me perfectly. The newest men’s wear clothiers don’t pretend, however, that their designs are inspired by – or borrowed from – their boyfriends’ closets. They’re made for women like me – and we are the boyfriends.

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