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6 Ways to Style Oversized Shirts

When you borrow (steal) one from your boyfriend.

street style  paris fashion week   menswear springsummer 2020  day three
Edward BerthelotGetty Images

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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Denim Shirt
Polo Ralph Lauren saksfifthavenue.com

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

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Ripped Loose Fit Jeans
AGOLDE nordstrom.com

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

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Strappy Leather Sandals
Mango mango.com

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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Gold Chain Marta Necklace
Jennifer Zeuner jenniferzeuner.com

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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Relaxed Kimono-Shape Sleeve T-shirt
COS cosstores.com

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

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Oversized Ex-Boyfriend Shirt in Romana Plaid
Madewell madewell.com

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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Le Vintage Bermuda Frayed Denim Shorts
FRAME net-a-porter.com
$100.00 (50% off)

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

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Azur Ankle-Wrap Snakeskin-Embossed Metallic Leather Sandals
Aquazzura saksfifthavenue.com

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

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Oval Flat Lenses
Ray-Ban ray-ban.com

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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Tie-Dye Cotton Shirt
Prada modaoperandi.com

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

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Knit Crop Top
ZARA zara.com

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

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Loose Mid Rise Jeans
& Other Stories stories.com

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

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Square Heel Sandals
JAGGAR shopbop.com

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

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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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Metallica Harvester of Sorrow Tour Glitter Tee
Urban Outfitters urbanoutfitters.com

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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Originals High Waist Loose Jeans
RE/DONE nordstrom.com

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

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Baby Frank Belt
B-Low the Belt shopbop.com

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

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Ray Tracer Sneakers
Fila shopbop.com

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

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Black Mini Attica Backpack
Alexander Wang ssense.com

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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Angie Textured Crepe Wrap Blouse
Cecilie Bahnsen modaoperandi.com

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

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High Waist Slim Kick in Coated Black
7 For All Mankind 7forallmankind.com

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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Intrecciato Weave Sandals
Bottega Veneta farfetch.com

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

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Fringy Crystal Bag
Les Petits Joueurs lespetitsjoueurs.com

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

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Christian VierigGetty Images
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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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Oversized Dropped-Shoulder Shirt
Raey matchesfashion.com.uk

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

Les Petits Jouers
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Katlyn Trousers
Stella McCartney farfetch.com

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

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