DORÉ

A couple of weeks ago I had dinner with one of my more fashionable friends and the guy she’s dating. She always looks good but that evening I was particularly struck by her effortlessly cool ensemble. “Oh yeah this is his shirt,” she said while tugging at a just-oversized-enough button down, “and he’s wearing my tee.” “Wait, are you wearing his jeans too?” I was met by some coy looks and shared giggles. I rolled my eyes, the dinner went on, but the image stuck with me.

I love when women pull off men’s clothes. Remember those old ads for The Kooples? Remember Kate Moss posing for Calvin Klein in Marky Mark’s jeans? Remember when boyfriend jeans became a thing? Boyfriend sweaters? J.Crew “boyfriend-themed” clothing mania? As a woman who has been single for much of her adult life, I can tell you that you don’t need to have a boyfriend, or want a boyfriend, or be interested in dating men at all to pull off this look. You just need to get your hands on some perfectly oversized clothes.

After my inspiring dinner encounter, I wanted to test out some similar styling on a real-life couple. Enter Elena and Tom, who are really just too good-looking and too cool to be real (except for that they are real and still really cool). On a sunny day in their Clinton Hill apartment we played around with some men’s clothes and their cute dog, Ace.

Individual styling is definitely key here. For example, I’m on the shorter side, so I prefer to balance out something oversized with something tighter, like a baggy pair of jeans with a more form-fitting top (extra points if you roll the waistband of the jeans 90s-style). For some women, adding a waist, by tucking a shirt or adding a belt can be helpful. Mixing in a feminine element, like a chic earring, to elevate a rugged tee or jacket looks cool too.

That being said, I’ve seen plenty of girls ignore every so-called fashion rule and look amazing. The most important styling tip I can offer, and perhaps the entire reason I’m attracted to this look, is that it’s all about the attitude.

Tom and Elena’s Jackets, Rag & Bone; Elena’s T-shirt, Shaina Mote, Earring, Sophie Buhai; Tom’s Jeans, A.P.C.; Elena’s Jeans, Her Own

Jacket, 3.1 Phillip Lim; Tank, Toteme; Jeans, The FEEL Studio; Earrings and Necklace, Sophie Buhai

Elena’s Sweatshirt, Everlane; Elena’s Jeans, The FEEL Studio; Elena’s Loafers, Redone + Weejuns; Tom’s Jacket, A.P.C. Tom’s T-Shirt and Jeans, His Own

Jacket, Rag & Bone; Pants, 13 Bonaparte; Earring, Sophie Buhai