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14 Ways to Wear Your Beloved Sweatpants Outside

How to create cute outfits with sweatpants is a question that will define 2020 and—most likely—2021, thanks to much of this year having been defined for many of us with strict shelter-in-place orders, sales of sweatpants were up 80 percent in April. And our commitment to comfort doesn’t seem to be slowing down, even as some of us are venturing outdoors to run errands, grab a bite, or to ease back to work outside the home. Because, really, after eight long months in elastic waists, who has the patience to wriggle into stiff jeans or fussy dresses? The challenge: Taking pieces you wear on the couch and turning them into cute outfits with sweatpants that make you feel like yourself back when getting dressed was something you actually had to think about and maybe even looked forward to.

Here, we found 14 women who perfected the art of cute outfits with sweatpants by styling them in a way that looks both comfortable but also cool and effortlesly put together. Maybe it’s adding a great overcoat or a matching sweatshirt, or maybe it’s slipping on a pair of high heels (bravo if you remember how to walk in them!) and carrying your favorite bag. Maybe it’s throwing on staples you’d normally pair with jeans or trousers such as a tailored blazer or a button-down blouse. Whatever route you decide to take, these these just-casual-enough outfits will definitely provide a little fashion inspiration as we move into the fall and winter and continue to wonder how to wear sweatpants all. The. Damn. Time. Just remember your mask. 

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Christian Vierig

A baseball cap, a cozy jacket, and a great pair of chunky boots all make a basic pair of sweatpants look downright chic. Designer bag optional.

Madewell Walton Shirt Jacket

ASOS Design Aqum Leather Chunky Boots

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Christian Vierig

Bright-colored sweats, heels, and a great bag are definitely an unexpected look but it works. 

Sub_Urban Riot Cambridge Crop Sweatpants

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Streetstyleshooters

Keep things simple in a matching cream-colored sweatsuit and black accessories. 

Coach Parker Convertible Backpack 16

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Christian Vierig

A furry coat and “fancy” bag is a cool way to balance out athletic sweatpants and chunky sneakers. 

Adidas Ozweego Cloud Sneaker

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Streetstyleshooters

Cuffed track pants and a duster cardigan looks perfectly appropriate for work or a fall stroll. 

Under Armour Women’s UA Rival Pants

Free People Stay Here Cardi

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Christian Vierig

Bold sweatpants and a fuzzy cropped cardi is a surprisingly cute combo. 

Camila Coelho Toni Cardigan

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Christian Vierig

Just add a blazer, killer accessories, and some low heels to your sweatpants for a polished ‘fit. 

Halogen Brushed Teardrop Earrings

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Hollywood To You/Star Max

Tie dye sweatsuits forever!

Tie Dye Cropped Sweatshirt

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Christian Vierig

Add heeled boots and an overcoat to a basic sweatsuit. 

Monday 7 Days Crewneck Sweatshirt

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Jeremy Moeller

Try tucking in a crisp button down to your classic sweats for an unexpectedly polished look. 

Uniqlo Supima Cotton Stretch Long-Sleeve Shirt

MWL Ribbed Seamed Sweatpants

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Kirstin Sinclair

Track pants pair well with work staples like a blazer, boots, and chic accessories.

Adidas Relaxed Track Pants

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Christian Vierig

Pastel sweatpants and a zebra coat because why not? 

Rachel Roy Zebra Wool Coat

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Christian Vierig

Just add a jacket of your choice when things get chilly.

Alo Yoga Accolade Sweatpant

Ten Sixty Sherman Padded Shoulder Tank

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Melodie Jeng

More-is-more never looked so cool. 

Aviator Nation 5 Stripe Sweats

Madewell Reversible Bucket Hat

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