From the Boys

5 years ago by

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.

From the Boys
From the Boys

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.



From the Boys



From the Boys
From the Boys
From the Boys
From the Boys

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


Add yours
  • I’m pretty sure Jason married me only to keep his clothes close.

  • I think of all the 90s flashbacks I’ve had over the past few years that the 90s have been cool again, this one takes the cake. The rolled jeans!! I used to borrow my Dad’s and do that. It was a terrible look on a short, hippy, short-legged person, but oh how I loved it.

    This is a gorgeous shoot, though, and I love the way the clothes are styled. I’m so often inspired by the way men wear their clothes – with such ease, movement, comfort, in a way that seems very elegant. At its best, women’s fashion can do the same, but we still have a lot to learn from the boys…

  • I think a lot of it has to do with the quality and comfort that traditionally male clothing provides. From my experience, the fabrics tend to be heavier, more solid, soft and last much longer.

  • I really liked this post, keep up the good work.

  • Anthony A. Cavanaugh November, 1 2018, 6:50 / Reply

    Hey I see old fashion really like that all things cover by you but now a days people like what on trending so check it out new one embroidered logo dress shirts for your new style cover or blogs.

  • People always gave me the weirdest looks when I buy men’s tees for myself, but the truth of the matter is that I like their fit and they look great over my skinny jeans. And yes, it’s definitely all about the attitude.

  • All the modern men’s clothes seem to be slim fit and women’s clothes now have to be oversize. It used to be the other way round, right? :)
    Men’s clothes often seem so much easier to pull off, I think.
    I love men’s shirts and have a few. Also I have men’s sweaters. It’s mainly because I shop vintage and come across awesome men’s stuff.

    I have wide hips so men’s clothes really don’t fit that well around them. But I’m small from the waist up so that helps! :)

  • I’ve been raiding my husband’s closet for yonks until I started shopping in men’s departament for myself. Now he steals from me and sometimes he get’s confused over whose coat he’s actually wearing :) I think boys clothes (especially on the high Street) are much better mas?, quality wise.

  • Lisa Walker November, 8 2018, 10:46 / Reply

    Love seeing this! Been dressing like this since I could shop a thrift store and raid my dad’s closet. Cheers to the 80’s! And cheers to Katherine Hepburn for all her inspiration, she was one of the big icons then.

  • very good continue like this, success

  • Hi,
    I’ve been assaulting my significant other’s storage room for yonks until I began shopping in men’s departament for myself. Presently he takes from me and now and again he get’s befuddled over whose coat he’s really wearing :)
    Gildan G200L Cotton T Shirt

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