When it comes to styling, we can always look to our favorite celebrities for the coolest ways to wear a trending piece. Case in point: cropped sweatshirt outfits. The athleisure staple is the perfect piece for when the weather’s not too hot or not too cold. However, with a piece as easy as this, it can be easy to fall into a bit of a style rut. Not to worry, as these style stars will give you just the sartorial inspiration you’re looking for.
As a piece that you can wear all year, depending on whether you layer it with other piece or wear it on its own, let these It girls show you exactly how a cropped sweatshirt can be worn. Whether you’re headed to the airport and need an outfit that can keep you comfortable during your flight or are heading out for the night and want a cool girl approved ensemble, this is one piece you want in your regular rotation.
See the looks now and then shop our favorites on the market.
If you’re looking to have more coverage, wear your sweatshirt underneath a pair of overalls for a cool, ’90s vibe.
Wear this for everything from your warm-ups and cooldowns to your days off from the gym.Available in sizes 1X to 3X.
Kith is a streetwear brand you need to know.Available in sizes XS to XL.
Want a cool look for a night out? A cropped sweatshirt paired with cool, distressed jeans will give you an edge that will get anyone’s attention.
All eyes will be on you—pun intended.Available in sizes IT 36 to IT 48.
This will look so cool layered under a denim jacket or overalls.Available in sizes 0X to 3X.
For a more dressed-up look, style your cropped sweatshirt with boyfriend jeans and heels. For an added layer, a trench coat will pull your outfit together.
Leave it to Rihanna to design a sweatshirt you’ll want to wear with everything.Available in sizes XS to XL.
Crushed velvet gives that extra edge of cool.Available in sizes 12W to 18W.
There’s nothing more classic (and comfortable) than the simple athleisure uniform of a cropped sweatshirt, leggings, and sneakers. Go monochromatic for a streamlined ensemble.
Perfect for any casual occasion.Available in sizes 12 to 28.
So soft and comfortable, this will make the best travel outfit piece.Available in sizes XS to L.
One of the greatest features of a cropped sweatshirt is that it makes the perfect throw-on-and-go piece when you’re on your way out. Style it with a pair of jeans and sneakers, and you can’t go wrong.
Off-White always has the coolest athleisure pieces.Available in sizes XXS to XL.
Wear this on its own or with a tank underneath.Available in sizes XS to XL.
For a simple outfit formula, a crewneck iteration of the trend will give your look a more polished appeal, especially if you style it with your standard black leggings.
Because everyone needs a classic crewneck sweatshirt.Available in sizes XS to XL.
For the hotter days, a short sleeve sweatshirt is all you need.Available in sizes XS to L.
When you’ve got comfort on your mind, style a cropped sweatshirt with a pair of wide-leg pants. Just thinking about this look makes us feel more comfortable.
These cutout details make this one of the coolest sweatshirts we’ve seen yet.Available in sizes XS to L.
Wear this to yoga and then to brunch afterward.Available in sizes XS to L.
Now, you have an arsenal of the coolest outfits to wear with cropped sweatshirts, whether you’re running errands or headed out for drinks.
-
It's Now or Never—54 Last-Minute Amazon Prime Day Deals You'll Regret SkippingElevated basics, celeb dupes, luxe-like styles, and more on sale.
-
Set Aside the Strapless Minidress—This Is the Trend to Choose If You Want to Look ElegantFrench Riviera approved.
-
I Spoke With Sofia Richie Grainge About Her New Amazon Line—These 23 Children's Items Are So CuteIf you're looking for chic baby clothes.
-
Hailey Bieber Already Wore the Denim Outfits That Will Define Fall 2025She's always setting the trends.
-
Oh Wow, Hailey Bieber's Go-To Denim Brand Is on Major Sale During Amazon Prime DayDon't miss out.
-
Not The Row, Not Khaite: The Affordable Wardrobe Basic Kendall Jenner Wears With Trousers Is on Sale on AmazonIt costs less than an iced matcha latte.
-
So Many Celeb-Loved Jeans Are On Major Sale RN—These 29 Are the StandoutsLevi's 501s: a Hollywood go-to.
-
Hailey Bieber Says Butter Yellow Is "Played Out"—Meet the Color Trend She's Backing InsteadIt's citrusy.
