12 Ways to Wear an Oversized Shirt

If the goal is cute and comfy, these outfit ideas are the perfect style solution.

While there's always room in our closet for tight, bodyhugging designs, such going-out dresses and leather leggings, we'll forever keep loose, baggy pieces as part of our rotation, too — specifically, oversized shirts. Somehow, this staple manages to be all the things: a breezy must-have for summer heat and roomy enough for winter layers. And while oversized shirts tend to be cozy and perfect for chilling on the couch, if you add a pair of heels or boots, they can instantly transform into something sexy.

No matter your personal style preferences, you'll likely find a handful of ideas for how to wear oversized shirts and make them part of your everyday look. Still, we've rounded up some inspiration to get you started, so whether you're hoping to keep it classic, dress up your loungewear, give things a western spin, or revamp an old button-down, here are our favorite takes on the trend, ahead.

01 of 12

Knot Your Average Shirt

how to wear an oversized shirt

Getty Images

An oversized tee or button-down tied into a crop top can really spruce up a look, and when styled with a long skirt or high-waisted trousers, it will accentuate your proportions. Bonus points if your bottoms also include a playful detail, such as ruffles or a pattern, which will add another element of fun.

02 of 12

Step It Up In Heels

how to wear an oversized shirt

Getty Images

An oversized top paired with shorts is well-suited for warmer weather, while heels help to make things less casual. This outfit could easily work for both a backyard barbecue or casually grabbing drinks around town.

03 of 12

Flex Your Muscles

how to wear oversized shirts
Christian Vierig/Getty Images

Go the minimalist route with an oversized muscle tee. Styled with baggy trousers or leather joggers and completed with sneakers or sandals, the result is effortlessly cool.

04 of 12

Start Simple

how to wear oversized shirts
Edward Berthelot/Getty Images

A larger, longer button-down or T-shirt can also double as a dress. Make the look monochromatic by adding a matching shoe, or swap them out for a more unexpected choice, such as some western boots. It's an easy outfit that still makes a statement.

05 of 12

Remember to Prep

how to wear oversized shirts
Edward Berthelot/Getty Images

If you're looking for a more playful way to wear a basic, oversized button-down, grab a structured or knit vest and layer it on top. Adding a tie is optional while bottoms are whatever you prefer, but either way, it'll give off a moody, academia vibe.

RELATED: Dark Academia Is the Literary Fashion Trend to Try Now

06 of 12

Try Traditional

how to wear oversized shirts
Jeremy Moeller/Getty Images

Of course, you can never go wrong with the timeless pairing of an oversized button-down and jeans. With a few buttons undone, including your cuffs, you're telling the world you're serious but can chill out, too. Whether you complete the look with boots, sneakers, or heels, all options are acceptable for brunch, date night, and the office.

07 of 12

Ready, Set, Match

how to wear oversized shirts
Melodie Jeng/Getty Images

An oversized shirt and matching bottoms create a pre-planned outfit that can be worn with any shoe you desire, whether you're into sneakers or slip-on loafers. Dare yourself to give things an off-duty twist and style it with a bralette during the summer months.

08 of 12

Tuck and Roll (and Accessorize)

how to wear oversized shirts
Edward Berthelot/Getty Images

On warm days, opt to tuck in your oversized graphic tee into an equally baggy pair of shorts. A chunky statement necklace and a structured jacket will help pull together the look for an easy transition from day to night.

RELATED: You're Probably Layering Your Necklaces Wrong

09 of 12

Let Loose

how to wear oversized shirts

Sometimes, we feel an urge to go baggy from top to bottom. This specific styling choice is incredibly comfortable and the closest thing to feeling like we have no clothes on at all. With a pair of slip-on sneakers, you can't get any cozier than this laid-back weekend outfit.

10 of 12

Top Things Off

how to wear oversized shirts
Christian Vierig/Getty Images

Unsurprisingly, an oversized shirt can act as a jacket for those crisp, in-between days, providing both warmth and an extra dose of style. Once it's layered over your look, you can choose leave it open or button it up before throwing on a few key accessories that will pull the whole thing together.

RELATED: 14 Shackets That Are So Cute and Cozy, You'll Wonder How You Ever Lived Without Them

11 of 12

It Takes Two

how to wear oversized shirts
Edward Berthelot/Getty Images

We're big fans of easy outfits that consist of just two pieces, so the lampshading trend will never not fly in our book. Take your oversized shirt or sweater and style it with over-the-knee boots. It's a sexy, sleek solution that works year-round, especially during those months when the goal is to keep your legs warm.

12 of 12

Show Some Skin

how to wear oversized shirts
Christian Vierig/Getty Images

If your button-down outfit is in need of a little spice, a quick trick is to unfasten the top and slip out a single shoulder. With the addition of elaborate jewelry, including pearl necklaces and drop earrings, as well as fancy footwear, you'll find this look works for a variety occasions — including more formal ones (just trade the jeans for bare legs, tights, or trousers).

Updated by
Samantha Sutton
Samantha is InStyle's senior fashion editor. She joined the brand in 2019 and oversees the site's fashion coverage, including trend reporting, fashion exclusives, celebrity style interviews, and Fashion Week coverage.
Related Articles