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Knowing what to wear with gray sweatpants — aside from the matching sweatshirt, if you own a full set — is a challenge. Styling an outfit that feels fashion-forward, unique, and elevated all at once is easier said than done. Most of us think of our perfect gray sweatpants as the ultimate loungewear, after all. They’re the answer to Netflix-and-chill Friday nights and sluggish Sunday mornings. But this fall and winter, your gray sweatpants outfit is getting a makeover. Whether you’re headed to the movies, brunch, or out to a bar at night (in heels), all of the looks ahead are proof that gray sweatpants can appear polished enough to impress.

If your goal is to show off a colorful and splashy new investment bag, take a cue from Shanina Shaik. The Australian supermodel kept things mostly sporty and neutral-toned, adding a single pop of color with her purple nylon purse. Meanwhile, there are also ideas here for how to wear your gray sweatpants with everything from a crop top to ballerina flats, which are the comfortable walking shoe du jour.

After you take in the smart ideas for outfits with gray sweatpants ahead, shop some slacks that will help you achieve the aesthetic you end up favoring most. From joggers that are tapered at the ankle to high-waist flares with an adjustable elastic waistband, trust that you’ll be hitting the street in a gray sweatpants outfit to make everyone jealous in no time at all.

Sarah Wasilak

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