14 Ways to Wear an Oversized Shirt (2024)

Oversized shirts have taken over and we've never been happier. After all, it's not every day that a fashion trend looks good and feels good to wear, too. But whether you're reaching for a fun graphic tee or a classic button-down, an oversized shirt is the perfect blend of comfort and style. Of course, since this fit naturally leans casual, there's a fine line between your oversized shirt outfit looking intentional versus downright sloppy; meaning, knowing how to style this item is a must.

So to help you out, we've rounded up 14 ways to wear an oversized shirt that will have you looking like a street style star.

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Start Simple

A monochromatic matching set will tidy up your loose-fitting look. Finish with a matching heel or consider a more unexpected choice, such as western boots. It's an easy outfit that still makes a statement.

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Knot Your Average Shirt

An oversized tee or button-down tied into a crop top can really spruce up any style. And when worn with a long skirt or high-waisted trousers, it can hug your curves in a way you'd only expect from a bodycon dress.

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Remember to Prep

If you're looking for a trendy way to wear a basic, oversized button-down, grab a structured or knit vest and layer it on top, prep school style. Adding a tie is optional while bottoms are whatever you prefer, but either way, you'll nail the light academia aesthetic.

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Go Classic But Modern

An oversized top paired with shorts is an all-weather go-to for a reason. When deciding on a color palette, a black-and-white outfit is classic and coordinated — but attention to detail will keep it from feeling stale. A zebra print skirt and mismatched footwear add a playful spin.

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Tuck and Accessorize

On warm fall 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.

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Flex Your Muscles

Go the minimalist route with an oversized muscle tee. Styled with baggy trousers or leather joggers, it reads as effortlessly cool. Try it the next time you head out for after-work drinks.

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Try Traditional

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.

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Ready, Set, Match

An unbuttoned oversized shirt with matching bottoms and an exposed bra is coordinated and sexy. The best part? It can be worn with any shoe you desire, whether you're into sneakers or slip-on loafers.

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Let Loose

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.

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Top Things Off

Unsurprisingly, an oversized shirt can act as a jacket — or rather, a shacket — 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 to leave it open or button it up before throwing on a few key accessories that will pull the whole ensemble together.

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It Takes Two

We're big fans of easy outfits that consist of just two pieces, so the lampshading trend is right up our alley. 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.

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Show Some Skin

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 of occasions—including more formal ones (just trade the jeans for bare legs, tights, or trousers).

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Cinch It In

Wearing an oversized shirt as a dress is something you might be familiar with if you grew up with older siblings or frequented thrift stores as a teen. This thoroughly modern update on the trend involved cinching an oversized T-shirt at the waist using a corset top. There are so many ways to make this look your own, but we particularly love a sheer long-line corset that lets any graphic on your tee shine through.

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All About the Layers

This outfit could easily work for an early fall apple-picking adventure — just opt for a rugged boot so you don't get your white sneakers mud-crusted. Layering a turtleneck underneath will look chic, not to mention, keep your neck warm, as well.