Stylish Sweatshirt and Shorts Outfits for Cooler Weather

This timeless outfit idea is perfect for these transitional months.

Model in sweatshirt with shorts and boots and Princess Diana in green sweatshirt with bike shorts, sunglasses, and an oversized tote bag.
Photo: Getty Images/InStyle

Getting dressed during the transitional weather months can be stressful. The dog days of summer can run into fall and the brisk winter chill can linger on into spring. If you think adding and removing layers are the only way to dress for indecisive weather, think again.

One stylish solution is the classic sweatshirt and shorts combo. For 60-degree days, and well into the 70s, this pairing proves to be warm enough to stop us from shivering, yet cool enough to keep us from sweating. Plus, you can always add an extra layer or two, switch up your shoe choice, and incorporate accessories to give this look a personal twist.

Here are a few more ways to wear this timeless transitional outfit.

01 of 07

Channel Princess Diana

princess diana in blue oversized sweatshirt and coral bike shorts with sneakers
Getty Images

Back in the '90s, the royal regularly relied on this combo, styling graphic sweatshirts with bike shorts, bulky socks, and sneakers. In recent years, this same outfit choice has become popular again, and you probably already have the items sitting in your closet.

02 of 07

A Set Makes Things Easier

gigi hadid in matching camel-colored shorts and sweatshirt outfit with khaki-colored beanie
Getty Images

At the same time, you can always go the Gigi Hadid route with a coordinating set. The model wore this camel option back in March 2022, adding a beanie for extra flair.

03 of 07

Grab an Additional Layer

emily ratajkowski in neon green sweatshirt, leather coat, black shorts, and mini uggs walking with cell phone in hand
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Some days are chillier than others, so if a sweatshirt alone won't cut it, throw on another light layer, like Emily Ratajkowski did with her leather blazer. Not only was it practical, it added even more interest to the look (along with those mini UGG boots).

04 of 07

Break Out Your Cutoffs

woman with blunt bob and sunglasses in screen print knit sweater with cobalt blue bag and denim bermuda shorts
Getty Images

Bermuda-length bottoms are perfect for in-between temperatures, since they provide more coverage, but the choice is really up to you. You can also cut a pair of jeans for this look and switch out your sweatshirt with a knit sweater or a long-sleeved tee, both of which work just as well with these bottoms.

05 of 07

Experiment with Shoe Choice

woman in white graphic sweatshirt, denim shorts, and white boots with a purple bag
Getty Images

Sneakers will turn this outfit into athleisure, while boots are a bolder, fashion-forward choice. Sandals will also keep things nice and breezy as the temperatures climb, and will allow you to take your sweatshirt and shorts combo into the summer months.

06 of 07

Elevate the Look with a Blazer

woman in a mismatched blazer with black bike shorts
Getty Images

If you're worried this outfit feels a bit too casual, or think it may be missing something, you can always add a blazer. The sharp, structured layer has the ability to pull almost any outfit together and make it feel more polished, even with bike shorts as your bottom choice.

07 of 07

Play Around with Accessories

person in lime green sweatshirt, long black shorts, a belt bag, back vest and durag
Getty Images

While you won't need to add much to this grab-and-go outfit idea, it doesn't hurt to incorporate your personal style and make it your own. Throw on a vest, show off your socks, carry a fun bag, or pile on necklaces and rings. A solid sweatshirt and shorts makes the perfect base, so go ahead and get creative with the extra details.

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