How to Wear Oversized Clothing
Style /
September 2022
There's a difference between clothes that look intentionally oversized and clothes that just look too big. To make oversized clothes look good, 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.
How can I make my oversized clothes look good?
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 honours) 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.
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."
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."
You need balance. When you're wearing big clothes, you don't want to look like you have a tiny pinhead
– Bettina Sapien, director of Global Brand Environment
How to style an oversized shirt
Knot it
Turn your oversized tee into a crop top with a simple knot to create a flattering look that accentuates your proportions. Pair with some high waisted jeans to give a sophisticated hourglass silhouette.
Tuck it in
Similar to knotting your shirt, you can tuck in an oversized shirt to give it more of a cropped appearance. This works especially well when combined with high waisted bottoms such as a jean skirt or a pair of high waisted jeans. If you’re struggling to find a shirt that’s loose enough, opt for a men’s shirt for a guaranteed oversized fit.
Keep things simple and accessorise
This is your go-to look if you want to wear an oversized shirt stylishly. There’s nothing that says ‘elegant and refined’ more than a neutral button-down shirt and mom jeans combo. If you want your jeans to be more on the baggy side, opt for some oversized men’s jeans and cinch them in at the waist. Finish off the look with chunky gold accessories and you’re good to go.
How to style an oversized hoodie or sweater
Pair with knee high boots
Channel your inner Arianna Grande by pairing your oversized hoodie or sweater with some heeled, knee high boots. Depending on the length of your sweater, you could opt for bare legs or choose to wear some cycling shorts underneath for an athleisure look. Take your pick from one of our women’s sweatshirts, sized up of course, or opt for a men’s sweatshirt for a looser fit.
Opt for slim-fitting bottoms
Since the top of your outfit is so loose and flowy, slim-fitting bottoms such as skinny jeans or leggings help to keep the outfit in proportion and add structure.
Try a denim skirt
For a preppy twist on the oversized sweater look, combine your sweatshirt or hoodie with a high waisted denim skirt. Most denim skirts are A line, so they fit close to your body. This makes them ideal to pair with an oversized sweatshirt. The key with this look is to have a good amount of the skirt’s fabric on show under the sweater—so make sure your sweatshirt isn’t too oversized.
How to style an oversized denim jacket
Layer over a crop top and cycling shorts
Playing around with different proportions can give you a flattering silhouette that just about any oversized jacket can achieve. Both men’s jackets and women’s jackets can be worn as oversized to make an outfit more interesting, and look best when worn open so the outfit underneath can be seen.
Try an oversized cropped denim jacket
If you’re after the oversized look but still want to show off your outfit underneath, a cropped denim jacket could be the wardrobe piece for you.