Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Christina Petruzzi
Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
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Photo: Allison Kahler.

Though sweatshirts once evoked visions of skater boys or lazy weekends spent inside, they’ve slowly become one of the most highly coveted, fashion-forward garments on the style scene. (Thanks, athleisure.)

These days, everyone from Versace to Givenchy has left their mark on the classic sweatshirt. And street-style stars have followed suit, creating eye-catching, elevated ensembles centered around this low-key loungewear staple.

MORE: The Utility Jumpsuit Trend Transcends Seasonality

Still, styling sweatshirt outfits requires a bit of finesse. Pair your go-to pullover with jeans and you risk skewing a little too pajama-friendly. Pair it with shorts, and you might look more 1980s athlete than 2010s trendsetter.

Being able to wear loungewear in public (and have it deemed legitimately fashionable) is a straight-up gift—and I’m not sure what we did to deserve it. But I’m of the mind that we should take full advantage of this movement while we can, while respecting the fact that it’s a privilege.

All I’m saying is: We’re lucky that sweatshirts are the trend du jour. And someday, in the foreseeable future, they probably won’t be. They’ll likely revert to their strictly loungewear status.

So let’s not abuse this power that’s been bestowed upon us. Let’s, instead, style our sweatshirt outfits with thought and care—so that we can postpone this inevitable reality as long as humanly possible. If our sweatshirt outfits are hella elevated, they can’t possibly sink back into the realm of sloppy hangover clothes, right?

MORE: 26 Not-So-Average Teddy Jackets to Shop This Fall

Naturally, we’ve turned to our favorite street style stars for a little inspo. These fashion-minded individuals have thoroughly mastered the elevated loungewear aesthetic, and we’re (obviously) taking notes.

Ahead, 17 sweatshirt outfits that are equal parts chic and cozy—and that are sure to leave a truly elevated mark on the sweatshirt trend.

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STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Hailey Baldwin

Hailey Baldwin took business casual to the next level by pairing her sweatshirt with a blazer, vinyl pants and cowboy boots.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Jourdan Dunn

Sweatshirts don't have to be oversized.

Photo: Robino Salvatore/GC Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

A belt will help your sweatshirt—in all its billowy glory—stay tucked into a skirt of your choosing.

Photo: Christian Vierig/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Model Gizele Oliveira proves sweatshirts are only made better by high heels.

Photo: Timur Emek/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Cardigans and sweatshirts don't have to be mutually exclusive.

Photo: Christian Vierig/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Pair your sweatshirt with a statement-making piece, like this asymmetrical skirt, for pure fashion magic.

Photo: Christian Vierig/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Tear-away pants are such a power move.

Photo: Melodie Jeng/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Juxtapose your go-to sweatshirt with a pleated skirt for a seriously dynamic look.

Photo: Claudio Lavenia/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Statement-making accessories can take a casual sweatshirt from chill to chic.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Monnochromatism works with everything.

Photo: Daniel Zuchnik/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Haven't you heard? Lampshading isn't dead.

Photo: Timur Emek/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Justine Skye

A cold-weather spin on summer's wide-leg crop trend.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Velour is totally on the menu.

Photo: Christian Vierig/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Belt bags and sweatshirts are a match made in sartorial heaven.

Photo: Christian Vierig/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Sweatshirt, trench, flare pants—can't lose.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

Pairing a ruffled skirt with a sweatshirt might sound so wrong, but this outfit is proof that it's very, very right.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

A blazer is a welcome addition to any ensemble (and an easy way to dress up your favorite pullover).

Photo: Christian Vierig/Getty Images.

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  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Hailey Baldwin
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Jourdan Dunn
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy | Justine Skye
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy
  • STYLECASTER | Your Definitive Guide to Wearing a Sweatshirt Without Looking Sloppy

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