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 (opens in new tab). Don't get me wrong, I love crop tops, (opens in new tab) bodysuits (opens in new tab), turtlenecks (opens in new tab), 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.
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.
Polo Ralph Lauren Denim Shirt
A good denim shirt is a wardrobe staple. Go a few sizes up to achieve that oversized look.
AGOLDE Ripped Loose Fit Jeans
Pair your oversized top with these relaxed fit jeans. The overall vibe is effortless and comfortable.
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.
Jennifer Zeuner Gold Chain Marta Necklace
Dress things up with this gold chain necklace—the perfect final element.
Femme Flannel
Your boyfriend's shirt, but make it chic. This flannel and oversized T-shirt combo is casual and cool.
COS Relaxed Kimono-Shape Sleeve T-shirt
Start with a basic black T-shirt (oversized, of course).
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.
FRAME Le Vintage Bermuda Frayed Denim Shorts
Offset your oversized top half with a pair of body-hugging Bermuda shorts.
Aquazzura Azur Ankle-Wrap Snakeskin-Embossed Metallic Leather Sandals
These stappy sandals add a feminine touch to a menswear-inspired outfit.
Ray-Ban Oval Flat Lenses
Finish off the look with some cool sunnies.
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.
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.
ZARA Knit Crop Top
This knit bralette adds a sexy touch when worn underneath the boxy shirt.
& Other Stories Loose Mid Rise Jeans
Add a pair of straight-leg white jeans to complement the tie-dye shirt.
JAGGAR Square Heel Sandals
Finish things off with a comfortable pair of square-toe sandals.
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.
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.)
RE/DONE Originals High Waist Loose Jeans
Pair your band T-shirt with these RE/DONE high waisted jeans, a favorite among It girls.
B-Low the Belt Baby Frank Belt
Add a Western-inspired belt to will highlight your waist.
Fila Ray Tracer Sneakers
Add a chunky dad sneaker, another model off-duty staple.
Alexander Wang Black Mini Attica Backpack
Stay hands-free with this black mini backpack with sleek chain details.
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.
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.
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.
Bottega Veneta Intrecciato Weave Sandals
Add a pop of color with these Bottega Veneta blue sandals.
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.
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.
Raey Oversized Dropped-Shoulder Shirt
Try wearing this top with a few buttons open, since this look is a loose one.
Stella McCartney Katlyn Trousers
Pair these cream linen trousers with your white top for a great neutral look.
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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