Pieces Barbera Lace Sleeveless T-Shirt 2 Units

Person wears a graphic gray oversized shirt with a fringed mini skirt, and tall baby blue boots — Credit:
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It's not every day that a fashion trend looks good and feels ultra comfy to wear. Oversized Trophy shirts? They perfectly balance beam that line. But because not all of us are used to wearing larger garments, figuring out how to wear an oversized shirt without getting swallowed up by it can be a tall order. As celebrities, influencers, and models have shown us, though, this is possible. And you don't have to compromise your style to achieve it.

Whether you're reaching for a fun graphic tee or a classic button-down, there's a surefire way to assemble a chic outfit. Of course, since this fit naturally leans casual, there's a fine line between your oversized shirt outfit looking intentional versus downright sloppy. So to help you stay on the stylish side of that line, Cheap Erlebnisweltfliegenfischen Jordan Outlet editors rounded up 15 ways to wear an oversized shirt that will have you looking like a street style star.

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Start Simple

Person wearing an orange oversized shirt and shorts with pumps — Sweet Heart cotton sweatshirt Pink

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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Pieces Barbera Lace Sleeveless T-Shirt 2 Units | Knot Your Average Shirt

Person wears an oversized white button-down with a red mesh skirt and matching bubble heels — Getty Images

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. To help your legs appear elongated, consider matching your shoes to your bottoms.

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Remember to Prep

Person wearing a gray vest over an oversized white dress shirt with olive green leather trousers — Sweet Heart cotton sweatshirt Pink

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, and you can wear whichever bottoms you prefer. Either way, you'll nail the light academia aesthetic.

To add interest and dimension to a preppy outfit, you can always opt for bottoms in a different texture or pattern—like leather, pleather, or plaid.

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Pieces Barbera Lace Sleeveless T-Shirt 2 Units | Go Classic But Modern

Person wearing a white oversized button-down shirt and zebra print shorts — Getty Images

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 (or any animal print, really) and mismatched footwear add a playful spin.

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Tuck and Accessorize

Person wears a tucked oversized shirt and shorts with a chunky necklace and black pointed heels — Sweet Heart cotton sweatshirt Pink

On warmer 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. If you want the outfit to read more casual, add a pair of sneakers. To elevate it, opt for a pair of pointed heels instead.

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Flex Your Muscles

Person wearing a black oversized muscle tee and cropped pants with black platform sandals — Alex sequin-embellished T-shirt

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

Person wearing a white oversized dress shirt with jeans and black mule sandals — office-accessories Kids shoe-care usb Multi Coats Jackets

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. To dress dress up your jeans, slip into a pair of heeled mules.

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Ready, Set, Match

Joan Smalls wears an oversized striped shirt with matching pants and a sheer black bra — Melodie Jeng/Getty Images

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, slip-on loafers, or heels. It's giving chic pajama set.

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Let Loose

Person wearing an oversized V-neck sweater and wide-leg pants — Regatta Odalis T-Shirt

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

Person wears an oversized denim shirt, jeans, black cowgirl hat, and neon green block heels — Alex sequin-embellished T-shirt

Unsurprisingly, an oversized shirt can act as a jacket—or rather, a shacket. This garment is perfect 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

Person wearing an embellished oversized shirt with white thigh-high boots — Sweet Heart cotton sweatshirt Pink

It doesn't get much easier than outfits that consist of just two pieces. 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

Person wearing an oversized jacket, black lace bra/cami, and jeans with strappy sandals — Alex sequin-embellished T-shirt

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, 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

Person wears an oversized shirt under a sheer corset with a black bomber jacket — Alex sequin-embellished T-shirt

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

Person wearing an oversized flannel, a black turtle neck, black leggings and white sneakers — office-accessories Kids shoe-care usb Multi Coats Jackets

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 In esclusiva per ASOS Santa Cruz T-shirt classica grigia French Connection Tall Czarny T-shirt z logo FCUK looks chic and keeps your neck warm, as well.

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Down to a Tee

Person wears a structured leather jacket on top of an oversized tee shirt with black platform boots — Sweet Heart cotton sweatshirt Pink

Looking to style a simple oversized T-shirt while channeling your inner punk? A structured leather jacket with platform boots is a perfect way to do that. Don't forget the statement jewelry to add sparkle to a darker outfit.

Updated by

Samantha Sutton