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My breakthrough moment happened last fall when I stopped into Phillip Lim's SoHo boutique in New York. After finding success with a pair of jodhpurs, I wanted an oversized sweater. But the women's versions felt too girly. That's when the sales associate told me that he often suggests men's wear to his female shoppers.

Lim is beloved as much for his softly tailored blazers and men's knitwear as for his effortless dresses. The marigold cardigan from the guy's side of the store was exactly what I wanted.

These days, it's fashionable to market “boyfriend” style to women. Relaxed-fit “boyfriend jeans” are favourites among celebs, while boxy “boyfriend blazers” worn with the sleeves rolled up are a looser alternative to stuffier styles.

But these looks are imposters. Far better to have fun with the real thing, from ties to trenches to man bags.

Women have a long history of borrowing from men's closets. Tie-wearing à la Annie Hall or Avril Lavigne is a way to push masculine-feminine buttons, while “boy shorts” share DNA with tighty whities. For some women, it's about gender politics; for others, it's a means to get home in the morning without putting on last night's party dress.

“Some girls have always looked at the men's stuff, but now a lot more girls are looking,” says Tania Matins, co-owner of Carte Blanche, a hip boutique on Toronto's Queen Street West.

Martins wears her boyfriend's rock and roll T-shirts, which she pairs with skinny jeans. By adding a pair of heels or ankle boots, she makes the look less masculine. “I have always liked the idea of mixing something not so fitted with something tighter and playing on the ‘macho feminine' look,” she says, noting that it takes a “very fashion-y” girl to pull this off.

This, however, is not just for girls, but for any woman who wants to make an individual style statement. “It's a great way to find clothes that you know you're not going to see on many other [women],” notes Siofan Davies, an assistant research editor at Fashion magazine who credits her tomboy past for her love of men's shirts and sweaters.

By pushing lean silhouettes, men's designers are making it easier than ever for women to fit into the clothes: Deejay Samantha Ronson and actor Katherine Moennig, who plays Shane on The L W ord, wear Dior Homme better than actual hommes.

Sydney Mamane, whose namesake Toronto store is a destination for directional men's fashion, says women have shopped there since the day he opened three years ago.

“They're not looking for dresses, that's for sure,” he says. “They're looking for things that are a bit more androgynous – looser, rounder silhouettes.”

Mamane says he makes his buying decisions based on what he likes rather than the gender of his customer. “Some of it happens to be a bit on the feminine side because, aesthetically, I like to see those crossover pieces in the store.”

For Rachel Matlow, an associate producer at the CBC, what matters is that the clothes fit well, no matter what department they came from. This means that she will buy boy's shoes but women's jeans.

Matlow feels that women shouldn't let concerns about appearing too manly discourage them. “It's about owning the look,” she says. “If you're a feminine girl who likes girl's things, you can put on boy's clothes and they may even make you look more feminine.”

Guys, meanwhile, don't seem to have quite the same latitude. Perhaps that's why denim brands are introducing “unisex” skinny styles.

Just don't expect “girlfriend” jeans any time soon.