9 Stylish Ways to Dress Up a Sweatshirt

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Published Feb 3, 2017

You know that feeling after a long day of work? When you slip off your heels, pull on your favorite sweatshirt and sink into the couch? Well, what if you could feel like that all the time and look fabulous while you’re doing it? Here, nine super-chic ways to rock a cotton crewneck in the daylight.

Walk in Wonderland

With A Blazer, White Tee And Jeans

Yes, you can wear a sweatshirt to work. Keep it business casual with a knit top underneath (the ultimate button-down illusion) and polished blazer on top... It’s sorta like your pullover sweater but with a little edge.

Get the look: Loft blazer ($128); L.L.Bean sweatshirt ($40); Mossimo T-shirt ($15); Paige jeans ($199)

Christian Vierig/Getty Images

With A Duster Coat, Button-down, Leggings And Sneakers

Layering 101: Draping a duster coat over a graphic crewneck and button-down equals total badass. Plus, a longer shirt underneath means you can totally get away with the whole “leggings-as-pants” look.

Get the look: Lauren Ralph Lauren coat ($220); Zumiez sweatshirt ($68); Madewell shirt ($75); BP leggings ($24)

Christian Vierig/Getty Images

With Skinny Jeans And Heels

Who said sweatshirts can’t be sexy? A pastel hue—paired with heeled slingbacks and your favorite denim—says you’re sorta trying but also totally playing it cool.

Get the look: Todd Snyder x Champion sweatshirt ($128); Frame jeans ($239); Jeffrey Campbell heels ($135)

Bisous Natasha

With A Leather Skirt And Tights

Play up your graphic sweatshirt with a miniskirt and heels for a girls'-night-out ensemble that's both comfy and stylish. Just be sure to keep colors and patterns to a minimum to avoid looking a little too hokey.

Get the look: Kenzo sweatshirt ($270); Topshop skirt ($55)

Hello Fashion

With Leather Leggings And High-tops

Reminder: Bookmark for your next airport rendezvous. Balance a baggy sweatshirt on top with leather skinnies down below to keep from skewing too “snowman.”

Get the look: Adidas sweatshirt ($55); Free People leggings ($74); Sorel shoes ($97)

Collage Vintage

With A Midi Skirt, Chunky Heels And A Clutch

For dressier occasions, tuck your topper into a pleated skirt. Then, rolled sleeves, a fold-over clutch and lace-up heels are the finishing touches to your Sunday-brunch ensemble.

Get the look: Hanes sweatshirt ($9); ASOS skirt ($46); See by Chloe shoes ($355)

Viva Luxury

With White Denim And Black Heels

Elevate any crewneck by keeping things simple and elegant on bottom. We love the contrast of a pair of white skinnies and matte-black heels.

Get the look: H&M sweatshirt ($30); Vince Camuto jeans ($69); M.Gemi shoes ($248)

Damsel in Dior

With A Pencil Skirt And Heels

Not all sweatshirts are created equal, however. Velvet or sequin embellishments mean you can really kick things up a notch. Try balancing out a bulkier number with a fitted pencil skirt for the ultimate office-to-happy-hour uniform.

Get the look: Nation LTD sweatshirt ($118); Diane von Furstenberg skirt ($248); Hayden Lasher purse ($1,500)

A Piece of Toast

With Dark Jeans And Slide Loafers

Regardless of whether it’s a food baby or—ya know—a real baby, pair your crewneck with dark denim and your most comfortable flat mules to channel all the loungey vibes. Oh, and rejoice in the fact that you could (and should!) rock a sweatshirt for the rest of your life...and look damn good doing it.

Get the look: Pam & Gela sweatshirt ($185); AG maternity jeans ($215); Gucci shoes ($695)

Roberta Fiorito

Director, Branded Content + Cohost, Royally Obsessed Podcast

As Director of Branded Content at Gallery Media Group, Roberta helps oversee the ideation and execution of sponsored content and experiential campaigns across PureWow and ONE37pm, including PureWow’s 24 in ’24. She began her career in editorial nine years ago, and has written and edited countless articles on news, trends, fashion, beauty and the royal family. She’s also cohost of the Royally Obsessed podcast, named one of the best royals podcasts by The New York Times and Town & Country. She cowrote the book Royal Trivia: Your Guide to the Modern British Royal Family.

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