Stylish Ways to Wear Your Favorite Sweatshirt

If there’s one fashion trend we hope doesn’t go away any time soon, it’s athleisure. It has become acceptable to wear sweatshirts, sneakers, leggings, and anything else that qualifies as comfort-chic to do just about anything. Does it get any better than that? But while it continues to show up on runways and in street style shots, athleisure has actually been explored by designers since the 80s, especially with regards to the sweatshirt.

“The sweatshirt has evolved from the Jennifer Beals ‘Flashdance’ version with its scissored and rolled neckline and the iconic exposed shoulder to the ultra-sexy Juicy Couture sweat suit with every girl rocking ‘Juicy’ on their twerker,” says Ty-Ron Mayes, a celebrity stylist who appeared on America’s Next Top Model. “Now, just about every luxury brand has gotten into the business of glamorous sweats. From the high-tech, sublimation versions of both Alexander Wang and McQueen to graphic prints from Balmain to the irreverent artistic sweatshirts from Jeremy Scott or the emoji style tiger motif of Gucci, sweatshirts continue to evolve because they are highly in demand.”

Your favorite pullover may not be designer and that’s okay. Old and oversized, cute and cropped, logo hoodies—the beauty of this trend is that it’s meant to look effortlessly chic. Here, top stylists tell us how to dress up a sweatshirt.

Consider geometry

Oversized or cropped, Rosaliz Jimenez, fashion director at Dia&Co, recommends taking the shape of your sweatshirt into account as you style the rest of your outfit. “Don't get swallowed by a bulky sweatshirt—instead, opt for one that is cropped and pair with a skirt in a silhouette that makes you feel beautiful,” she adds. “Pencil or A-line—either will work as long as it's worn high on the waist.”

Or, you can follow in Rihanna's footsteps and opt for an oversized hoodie worn as a dress. “Grab a hoodie from the menswear section or borrow your boyfriend's and pair it with heels,” Jimenez says. “Skip the pants this time! It's almost like staying home on the couch.” Whatever you choose, try your best to avoid going too casual for risk that it might appear sloppy. Finish the look with statement shoes and accessories.

Play with texture

Adding a bit of texture is a quick way to dress up sweatshirts, says Patrice J. Williams, an on-air style expert at Looking Fly on a Dime. “This can be as simple as adding on layers, which provide fashion and functional warmth,” she says. An easy style formula for beginners is a button-down shirt that hits just below the waist with the collar peeking out at the sweatshirt’s neckline. “Just make sure each layer is of varying lengths, so they all get their shine and don't add bulk,” Williams warns.

Another easy way to layer is with a zip-up hoodie under a jacket. “Pick out the jacket that calls to you, be it a tweed blazer, a leather moto, denim jacket or anything in between, and complete the look with an office-friendly pencil skirt or slim-fitting trousers,” says Jimenez, adding that the hoodie can be worn unzipped over a slouchy t-shirt for even more edge.

Don’t be afraid of detail

Another way to take your sweatshirt to the next level is by adding flashy detail. This is a fast and simple way to create a completely new look that crosses daywear to eveningwear, explains Mayes. “Try layering with a statement necklace, pushing up those sleeves and adding an oversized watch or a stack of bracelets,” he says. “Or, hit your local department store with a plan to make your sweatshirt sparkle and shine with a collage of brooches or studded epaulets placed on the shoulders for a high fashion military look.” Pair the sweatshirt with a voluminous ball skirt and finish the look with a jewel encrusted clutch and metallic shoe. Instant glam.

Choose your shoes wisely

“Don't be afraid to rock a sweatshirt by pairing it with sexy thigh-high boots or over-the-knee socks and ankle boots,” says Kimmie Smith, a celebrity fashion stylist in New York City. “Pairing a sweatshirt with great shoes makes the look more put together versus the I-just-rolled-out-of-bed look,” she says. She warns not to finish your outfit with flip flops or flats, as these do little to elevate the look. Go for boots, stilettos, or stylish sneakers instead. “This seriously distracts from the fact that you're just wearing a sweatshirt,” Smith explains.