6 Different Ways to Style an Oversized Shirt

(Image credit: Edward Berthelot / Getty Images)

By Shelby Comroe 2021-06-05T22:47:04Z

Oversized shirts are my go-to off-duty staple; I often find myself perusing my boyfriend's side of the closet in search of that perfect menswear shirt. Don't get me wrong, I love crop tops, bodysuits, turtlenecks, any constricting (but cute) style—but sometimes comfort is key. There are days when a big, billowy shirt is the only thing I want to wear. But styling an oversized shirt can get tricky; no one wants to look like they're headed to bed. Below, I've broken down how to wear an oversized shirt in a few different ways. Whether you're stealing your boyfriend's flannel or rocking an old band T-shirt, there are so many different ways to style this piece.

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The Canadian Tuxedo

This is my personal favorite off-duty look. You can't go wrong with double denim, in my opinion. This look is season-less—swap out the sandals for boots and add your favorite jacket as we head into fall.

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Polo Ralph Lauren Denim Shirt

A good denim shirt is a wardrobe staple. Go a few sizes up to achieve that oversized look.

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AGOLDE Ripped Loose Fit Jeans

Pair your oversized top with these relaxed fit jeans. The overall vibe is effortless and comfortable.

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Mango Strappy Leather Sandals

Strappy sandals add a summery element to any outfit. Transition from day to night by swapping out the sandals for a pair of pumps.

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Jennifer Zeuner Gold Chain Marta Necklace

Dress things up with this gold chain necklace—the perfect final element.

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Femme Flannel

Your boyfriend's shirt, but make it chic. This flannel and oversized T-shirt combo is casual and cool.

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COS Relaxed Kimono-Shape Sleeve T-shirt

Start with a basic black T-shirt (oversized, of course).

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Madewell Oversized Ex-Boyfriend Shirt in Romana Plaid

This shirt is called the "ex-boyfriend" shirt for a reason. This oversized flannel looks like it came straight from his closet.

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FRAME Le Vintage Bermuda Frayed Denim Shorts

Offset your oversized top half with a pair of body-hugging Bermuda shorts.

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Aquazzura Azur Ankle-Wrap Snakeskin-Embossed Metallic Leather Sandals

These stappy sandals add a feminine touch to a menswear-inspired outfit.

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Ray-Ban Oval Flat Lenses

Finish off the look with some cool sunnies.

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Try A Print

Have some fun with a bold print. Wear this shirt open for an easy, breezy look. Offset the boxy shape with a feminine bralette and straight-leg jeans.

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Prada Tie-Dye Cotton Shirt

If you're looking to experiment with print, try tie dye—it's one of this season's biggest trends.

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ZARA Knit Crop Top

This knit bralette adds a sexy touch when worn underneath the boxy shirt.

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& Other Stories Loose Mid Rise Jeans

Add a pair of straight-leg white jeans to complement the tie-dye shirt.

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JAGGAR Square Heel Sandals

Finish things off with a comfortable pair of square-toe sandals.

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Off-Duty

Liu Han's outfit is model off-duty perfection, and it's very easy to recreate. Perfect for girls on the go, this look is super cool and comfortable. Throw on a leather jacket, strappy sandals, and some bold jewels to spice things up for the evening.

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Urban Outfitters Metallica Harvester of Sorrow Tour Glitter Tee

Start with your base: This oversized, vintage-inspired band T-shirt is perfect for that off-duty look. (Pro tip: Know at least one of the band's songs, just in case.)

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RE/DONE Originals High Waist Loose Jeans

Pair your band T-shirt with these RE/DONE high waisted jeans, a favorite among It girls.

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B-Low the Belt Baby Frank Belt

Add a Western-inspired belt to will highlight your waist.

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Fila Ray Tracer Sneakers

Add a chunky dad sneaker, another model off-duty staple.

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Alexander Wang Black Mini Attica Backpack

Stay hands-free with this black mini backpack with sleek chain details.

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Add Some Volume

Try out some bold volume with a balloon sleeve top. Style your ultra feminine shirt with leather bottoms to give the look a bit of an edge.

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Cecilie Bahnsen Angie Textured Crepe Wrap Blouse

This Cecilie Bahnsen top cinches in at the waist and billows out. It's oversized without completely losing shape.

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7 For All Mankind High Waist Slim Kick in Coated Black

Pair your flowy feminine top with a sleek pair of black-coated jeans. The leather look is edgy and suitable for a night out on the town.

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Bottega Veneta Intrecciato Weave Sandals

Add a pop of color with these Bottega Veneta blue sandals.

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Les Petits Joueurs Fringy Crystal Bag

Transition into the evening with this crystal bag—another great way to add a pop of color to your look.

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The Crisp White Button Down

Nothing screams "classic" like a crisp white button-down. If you're tired of the same old sundress, try out an oversized button down and a pair of linen pants. The look is breathable, comfortable, and chic.

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Raey Oversized Dropped-Shoulder Shirt

Try wearing this top with a few buttons open, since this look is a loose one.

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Stella McCartney Katlyn Trousers

Pair these cream linen trousers with your white top for a great neutral look.

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Paris Texas Python Print Platform Sandals

Spice things up with a python print platform sandal. Pro tip: If you don't have time to get your trousers shortened rock a pair of platforms.

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