3 Drawstring Shorts Outfits for Guys
By Gabi Meyers | Last Updated: Apr 20 2024 | 5 min read
There’s no single clothing item that sings, “Warm weather is here!” than shorts.
T-shirts? Love ’em, but 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 drawstring shorts. Thanks to their comfortable elasticized waistlines, they’re a real fan favorite style of shorts for guys. And hey, us ladies get it! We’re not wearing leggings for our health.
You’ll find three drawstring shorts outfits in this guide, perfect to wear all spring and into summer.
Casual and comfortable, yet totally stylish, a drawstring short in cotton or twill is the perfect addition to your spring and summer wardrobe.
Below, 3 drawstring shorts outfits for guys to wear:
for WFH
Shop the outfit:
- shorts: J.Crew
- sweater: Alex Crane
- bandana: Abercrombie
- sneakers: Nike
Wear it Well: When it comes to the right occasions for drawstring shorts outfits for guys, a regular ol’ work from home workday is pretty much perfect.
A lived-in sweatshirt over a short-sleeve Oxford shirt is a perfectly put together combination for Zoom calls, while the corduroy shorts look better than sloppy sweatpants if you need to dash out.
RELATED: 15 #SGapproved t-shirts for 2024
As for the footwear? I love these Saucony sneakers.
Don’t be afraid to pair them with tall crew socks. In 2024, we’re skipping the no-show socks in favor of something more visible. Yes, I said it!
weekend vibes
Shop the outfit:
- shorts: J.Crew
- tank top (3-pack): Pair of Thieves
- patterned shirt: Wax London
- shoes: Nisolo
Wear it Well: A pair of slippers I highly encourage you to wear out of the house!
These Nisolo woven slip-ons have become a warm weather men’s wardrobe staple.
As for the rest of the lewk, do not sleep on these funky tie-dye BDG shorts from Urban Outfitters.
With the band collar button-down up top, the outfit as a whole looks surprisingly sophisticated.
dressy casual
Shop the outfit:
- shorts: J.Crew
- long-sleeve shirt: Alex Crane
- quarter-zip pullover: Kiel James Patrick
- boat shoes: Sebago
Wear it Well: If you know anything about Team SG, it’s that we love a man in stripes!
RELATED: 3 Ways to wear the “nautical look”
Opt for a classic boat shoe, or go for something unexpected like huarache sandals to ensure you’re not veering into Kennedy cosplay with your outfit.
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 stylish and affordable drawstring shorts for guys:
Length: This style comes in 5″ and 7″ (cough go for the shorter style cough)
SG Says: This under-$100 pair is the perfect compliment to your summer tan.
I love the slightly faded coloring, which makes it look like you found the perfect vintage pair while thrifting.
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?
Length: 6 1/2″
SG Says: These affordable, classic cotton shorts are also available in nine different colors. You’ll barely have to do laundry this summer!
4. J.Crew, $70
Length: 6″
SG Says: These are the same shorts used in the outfits featured here. J.Crew’s dock shorts feel like you’ve had them forever, the first time you pull them on.
In a good way, of course.
If you’re covered for khaki and other neutrals, opt for tomato red, or a textured blue seersucker. They’ve also got a tech fabric style our season our team is pretty into.
More Great Style Stories from SG HQ
- The Guys’ Guide to Chinos
- Real Guy Style: Casual Loungewear Looks for WFH
- The Best 5″ Men’s Shorts
- How to Wear Adidas Samba Sneakers
Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.
