Collage of people wearing oversized clothing. Collage of people wearing oversized clothing.

How to Wear Oversized Denim

January 13, 2020

After a decade dominated by skinny jeans, denim is finally loosening up. There’s a difference between clothes that look intentionally oversized and clothes that just look too big. To do oversized right, read the advice in our monthly Staff Style column, where real Levi’s® employees show you how to wear the clothes they work on every day.

SIZE UP - WAY UP

“I’m probably a size 28 or 29,” says Bettina Sapien, our director of Global Brand Environment (aka our stores). “I’m only 5’2”. But I often wear a men’s 501® jean in a size 34 or 36. If you want big, you want real big.”

Sizing up will give you the oversized silhouette you want, but it’ll also give you a waist that’ll fall right off without some help. Our advice: either get the waist taken in (our Tailor Shop can do the honors) or cinch it with a belt for the proverbial “paper bag” look you see below on Ezra Price, our Brand Environment assistant manager, shown here wearing a 505.

“Initially I wanted a wide leg, so I had to buy that big size,” he says. “Then I started realizing that I actually enjoy how the paper bagging looks.” These days he buys his jeans eight sizes too big. And his Trucker Jacket is an XXXL.

Person wearing oversized denim jacket and oversized jeans.

TRUST YOURSELF

If at first your supersized clothes feel strange, avoid the urge to fidget. “I see a lot of women in particular try to roll up the sleeve when they’re trying on a Trucker Jacket,” Bettina says. “I say, ‘No, no. Leave it.’ Just own that sleeve halfway down your hand. It’s about having confidence.”

 

This may seem crazy when the whole point of the look is for it not to fit. “But there’s such a thing as fun oversized, versus it looking gross on you,” Ezra says. The key is for your look to always seem intentional. Maybe hem the bottoms like he does, so they land just above your sneakers and don’t look messy.

 

And remember, if you’re paper-bagging, you want to cinch at your natural waist — as opposed to low on your hips. “It looks a little odd if you have a big pocket hanging super low,” Ezra says. “I pull these almost up to my belly button.”

Person wearing oversized jacket with jeans.

ACCESSORIZE ACCORDINGLY

“The hat helps,” Bettina says. “You need balance. When you’re wearing big clothes, you don’t want to look like you have a tiny pinhead.”

GO ONE PIECE AT A TIME...

Maybe you don’t want a huge top and bottom. That’s cool. A single piece can still give you the look. In the photo above, Bettina wears an XXL sweatshirt over a pair of 501s® that she’s had patched and cropped at our Tailor Shop. “They’re close to the body, and I like the juxtaposition with a big top,” she says.

“I like to mix the proportions,” Ezra adds. “If I’m doing a baggy jacket and baggy jeans, my t-shirt might be pretty fitted.”

...OR JUST ONE PIECE, PERIOD.

One last look to consider: the oversized boiler suit. “I like the whole silhouette,” Ezra says. “It’s different. I grew up wearing skinny and slim jeans — everything fitted — and the older I got, the more comfortable I felt in oversized clothes.”

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