Might I Suggest: How to Make the Most of Men’s Clothing

As a team, we’re often fielding fashion-centric quandaries via Twitter, text and Instagram DM, so we figured, why not make it dot-com official? Welcome to Might I Suggest, the style advice column that solves your most elusive market searches and enduring style challenges. This week, Leandra answers this question from Instagram by community member, Kelly:

How can I make an outfit for myself with items from my boyfriend’s closet?

If the single piece of style advice my mother has ever passed down orally does, in fact, hold objectively true — that in order to look and feel good, you should figure out a way to get yourself a good pair of shoes because a) you need to leave the house and b) you can improvise the rest of your look with meager means — then I’d like to regurgitate it right here. Because these “meager means” don’t have to suggest you spend under $20 to buy yourself an outfit, they could (and do!) just as well refer to the creative ways you consider recycling. And one such recycling tactic sure as shit involves renting clothes from a man — any man: brother, dad, friend, co-worker, accountant — in your life.

The only requirement is that you know what you’re looking for, because shit could get weird if you dive nose first, blindfold on, into the cleavage of another’s wardrobe only to find yourself having emerged on the other end dressed as an employee of Dunder-Mifflin.

I did a bit of Instagram sleuthing, Kelly, because your account is not private, so I think I have correctly identified the man you call “boyfriend” and let me just say: I totally get why you’re asking this question!!! The striped henley! (Cotton and crewneck, so the unfamiliar can envision it.) His khaki pants! (They are constructed more like jeans, with skinny ankles.) You can wear these pieces together, roll up the pants, add a belt to make them high waist, then a pair of strappy ass sandals (jewel-encrusted should you please), and head the fuck out for a night on the town.

I also noticed a grey wool jacket that if you borrow, I have a hunch, will hit you in the exact same place that a mini dress ends thus creating a perfect marriage of man and woman, coat and skirt. Everything I just surrendered is pretty much the crux of my advice — take the regular clothes and soup them up. That means rolling up the bottoms of jeans, or pairing suit trousers with heels (brownie points if you are so courageous as to tuck said trousers into knee-high boots), scrunching the sleeves on his t-shirts, turning the long sleeves three-quarter length and the short sleeves…-less. If you’re borrowing a blazer, tuck the sleeves in from the inside (so, roll in, not out) so as to expose your wrists; this will make a disproportionate shoulder pad look more deliberate. You know?

And now for the fun stuff: A meet-cute between his wardrobe and yours.

If you’re rolling up his jeans or khakis, go for shoes that are slight — like a pair of ballet flats, or platform-free sandals/heels.

If you’re wearing his blazer add a skirt, and if you don’t feel like wearing a t-shirt under said blazer, try a dress, like one of the below (no pressure, but I’d probably opt for a legit nightgown under said blazer):

If you choose the t-shirt, and the one you select is his striped, crew-neck henley, add a necklace.

Do this if you’re borrowing a button down, too. But to this point: roll up them sleeves as if Jenna Lyons on set at J. Crew and unbutton the top the 3 buttons…or unbutton them all! Wear his shirt as a bathing suit cover-up.

(And speaking of bathing suit cover-ups, I almost forgot to mention that wearing his swim trunks are fair game with your slight sandals and bathing suit and sunglasses of your choosing.)

If you’re opting to wear his blazer and his shirt and his pants, don’t forget your investment shoes, and a tiny, almost useless handbag (you have so many pockets! It’s just for show):

This one, btw, does not strike me at all as useless, but it’s really cute.

And that’s that, people. But If you’d like to see a story that was published in like, 2013 wherein I dressed myself in my husband’s wardrobe, here-you-go.

Might I Suggest identity by Edith Young; Painting of Sir John Shurley of Isfield (1565–1632) via The Metropolitan Museum of Art. 

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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