Wear it Well: 3 Ways to Wear Drawstring Shorts

the perfect meeting between casual comfort and summer cool

By Gabi Meyers | Last Updated: Aug 12 2015

While the beginning of summer doesn’t *actually* happen until the 21st, I think we are all in agreement when June 1st means it’s time to go into summer mode. 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 ways to wear the drawstring short:


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

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

Wear it Well: 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. 

Tell Me:

Where would your drawstring shorts get the most wear?

Want to know how to wear more clothes more than one way? How to wear the nautical look and the color purple.