Casual Summer Style: 3 Drawstring Shorts Outfits for Guys

Casual comfort meets 2020 trend

By Gabi Meyers | Last Updated: Jul 17 2020

I’m just going to say it. There’s no single clothing item more quintessentially summer than your favorite pair of shorts, and we may have a new contender for that title.

Enter, the drawstring short.

Casual, comfortable and easily convertible for many occasions, the drawstring short feels like sweatpants, without being quite as sloppy.

Below, 3 drawstring shorts outfits for guys to wear this summer:


shorts: Katin, $50 | Shirt: River Island, $56 | Shoes: Bass, $79

Sunglasses: Oliver Spencer, $168 | Bracelet: Miansai, $65

Wear it Well: When it comes to occasions for drawstring shorts outfits for guys, a backyard hang session is pretty much the perfect opportunity.

Roll the hem on the shorts, and make sure you spill the BBQ sauce on the dark part of the patterned shirt. Don’t forget suede protector on the shoes!


Shorts: Obey, $59 | Tee: Deus Ex Machina, $44 | Shoes: Vans, $55 | Sunglasses: Ray-Ban, $210

Wear it Well: Pull the socks all the way up.


Shorts: La Panoplie, $105 | Shirt: Calvin Klein, $35 | Sweater: J. Crew, $112

Shoes: Johnston & Murphy, $155 | Watch: Fossil, $115

Wear it Well: Leave the shirt tails out – the sweater will add enough polish to let the shirt hang out. 

Shop #SGapproved drawstring shorts for guys:

1.Save Khaki, $110

Want to know how to wear more clothes more ways this summer? Check out how to wear a popover shirt five ways, and what to wear with white jeans.