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6 Ways to Style Oversized Shirts

When you borrow (steal) one from your boyfriend.

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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
$128.00

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
$188.00

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
$49.99

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
$220.00

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
$25.00

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

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Oversized Ex-Boyfriend Shirt in Romana Plaid
Madewell madewell.com
$39.99

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
$140.00

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
$825.00

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

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Oval Flat Lenses
Ray-Ban ray-ban.com
$155.20

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
$720.00

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
$19.90

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
$55.00

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

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Square Heel Sandals
JAGGAR shopbop.com
$164.00

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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Metallica Harvester of Sorrow Tour Glitter Tee
Urban Outfitters urbanoutfitters.com
$39.00

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
$265.00

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
$92.00

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

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Ray Tracer Sneakers
Fila shopbop.com
$75.00

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

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Black Mini Attica Backpack
Alexander Wang ssense.com
$485.00

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
$465.00

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
$119.00

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
$1,270.00

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

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Fringy Crystal Bag
Les Petits Joueurs lespetitsjoueurs.com
€590.00

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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Oversized Dropped-Shoulder Shirt
Raey matchesfashion.com.uk
£345.00

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

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Katlyn Trousers
Stella McCartney farfetch.com
$463.00

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

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