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.

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?

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.