Outfit Inspiration

3 Easy-Breezy Drawstring Shorts Outfits for Guys

Casual Spring and Summer Style for All.

By Gabi Meyers | Last Updated: Apr 12 2021

There’s no single clothing item that sings, “Warm weather has arrived!” than shorts. T-shirts? You can wear those under a sweater all through winter. Swim trunks? You’ve gotta wait ’til summer. But shorts? Shorts are ready to wear now. Today, we’re spotlighting the shorts of 2021 with three drawstring shorts outfits perfect for guys to wear.

Casual and comfortable, yet totally stylish, a drawstring short in cotton or twill is perfect for WFH (still) and slowly re-entering society this summer.

Below, 3 drawstring shorts outfits for guys to wear:

WFH

shorts: Abercrombie & Fitch, $59 | shirt: Todd Snyder, $56 | shoes: Sebago, $180

Wear it Well: When it comes to occasions for drawstring shorts outfits for guys, a regular ol’ work from home workday is pretty much the perfect opportunity.

A denim shirt is one of our team’s favorite spring style essentials, and that chunky boat shoe is easy to slip on before your first Zoom call of the day to help you get your head in the game.

on a boat

shorts | sweater: J.Crew, $178 | sneakers: Nike, $55

Wear it Well: If you know anything about Team SG, it’s that we love a man in nautical stripes!

RELATED: 3 Ways to wear the “nautical look”

Go ahead and wear the sneakers with no-show socks, or go bold with a calf-high pair.

weekend hang

shorts |sweatshirt: Todd Snyder, $98 | clogs: Birkenstock, $145

Wear it Well: Yes, clogs. We won’t stop until every SG reader has given in to this 2021 trend!

I mean, sure, you could swap out this trendy (but oh so comfy!) footwear for…well, really any other warm weather shoe, really. Boat shoes, white sneakers, even a Birkenstock sandal!

I know, I know. I’m reaching here. But a girl can dream!

As for the rest of the lewk, wear the sweatshirt over a t-shirt and under a denim jacket for extra stylish layering.

RELATED: 15 #SGapproved t-shirts for 2021

How to tie drawstring shorts

Don’t overthink it!

The same type of knot you use to lace up your sneakers works for drawstring shorts.

Just don’t leave the strings untied. It’ll look sloppy.

Shop drawstring shorts for guys:

1. Abercrombie & Fitch, $59

Length: 7″

SG Says: This under-$60 pair is also available in navy, dark grey, and khaki. But c’mon, this pink pair is so cool! And you know none of your friends will be wearing them.

2. Old Navy, $27

Length: 7″

SG Says: This Old Navy style has become a favorite of our personal stylists.

Not too expensive, just the right length, what’s not to like?

3. Save Khaki, $95

Length: 7″

SG Says: This under-$60 pair is also available in navy, dark grey, and khaki. But c’mon, this pink pair is so cool! And you know none of your friends will be wearing them.

4. Old Navy, $27

Length: 7″

SG Says: Yes, that’s the same style as the Old Navy pair above. But can you blame me for including them in one more colorway?

If you’re covered for khaki, try this charcoal color next.

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.