Relaxed Denim Shorts Are the Silhouette of the Summer—Starting With These 25 Pairs
I'll admit it: I avoided denim shorts for nearly a decade and would go so far as to say I was a bona fide hater. In my defense, the short cutoffs with low rises à la American Eagle were the only style option I had for many years, and if it wasn't already obvious, I'm not exactly a big fan of skintight denim shorts and actively avoided wearing them. All that is to say, I'm breathing a huge sigh of relief now that relaxed styles are becoming a thing. While those tighter fits are still out there, it's becoming increasingly easier to find looser-fitting shapes and shorts with more forgiving leg-opening measurements. (A good measure of thumb is roughly around 25 inches or higher for looser fits and around 21 inches or lower for tighter styles.)
Relaxed shorts are just so much easier to wear and the more comfortable option, but now, they've become the trendy way to wear denim shorts too. If you're on board with the relaxed look or are interested in testing the waters this season, I've pulled together my edit of the best relaxed denim shorts on the market, from a top-rated Levi's style to cool, minimalistic Bermudas. Since outfit curations are one of my favorite hobbies, I've included several styling ideas to inspire your outfit choices along the way.
These one of J.Crew's top-rated shorts styles, and I can see why.
I always look for how roomy shorts are in the leg, and this Mango pair looks like the perfect relaxed fit.
I love when a good shopping find comes with an even better outfit idea.
Shocking no one, Levi's is behind one of the summer's most in-demand denim shorts.
I love how these hit at a cool mid-length that's elevated and ultra-wearable.
These fall just above the knees for a sleek, minimalistic feel. Net-a-Porter suggests pairing these with strappy sandals, and I couldn't agree more.
I love how these sit lower on the hips for an even more relaxed look.
Madewell has perfected its '90s jeans, so it should come as no surprise that the brand has also mastered relaxed denim shorts.
I'm copying this look and wearing my Bermuda shorts with pretty ballet flats.
These are a great stepping stone between regular denim shorts and relaxed fits.
Mother never disappoints when it comes to denim.
The combination of this silhouette and wash is perfection to me.
I love how these relaxed shorts are styled with a button-down for a hint of polish.
This mid-length is great when you're not in the mood for revealing short-shorts.
This post was published at an earlier date and has since been updated.
Anna is an NYC-based senior fashion editor who has been a member of the Who What Wear team for over seven years, having begun her career in L.A. at brands like Michael Kors and A.L.C. As an editor, she has earned a reputation for her coverage of breaking trends, emerging brands, luxury shopping curations, fashion features, and more. Anna has penned a number Who What Wear cover interviews, including Megan Fox, Julia Garner, and Lilly Collins. She also leads the site’s emerging travel vertical that highlights all things travel and lifestyle through a fashion-person lens.
-
The New Rules of Summer Denim: No Rips, No Fray, No Fuss
See the full set of rules inside.
By Michelle Scanga
-
The Anti–Skinny Pants Trend Cool New Yorkers Are Quick to Ditch Their Blue Jeans For
Buh-bye.
By Eliza Huber
-
I Tried On All the Coolest Items From Grlfrnd—These Are the Things Worth Buying
I'm betting on denim.
By Sierra Mayhew
-
I Called the Cuffed Jeans Trend—7 Shoes Fashion People Are Wearing With the Chic Denim Style
Style the jeans like a fashion person.
By Jennifer Camp Forbes
-
Stop the Search—We've Discovered the Cool Denim Trend Every Fashion Person Will Be Wearing Throughout 2025
And 2026.
By Nikki Chwatt
-
I'm a Fashion Editor Who Loves Effortless Vacation Essentials—25 Gap Finds That Caught My Eye
Many are even on major sale.
By Jennifer Camp Forbes
-
People Are About to Ditch Denim Cutoffs for the Casual Shorts Trend That's More 2025
Important pre-summer reading.
By Allyson Payer
-
Watch Out: This Controversial Shorts Trend Is Bubbling Way Up
A micro-movement worth getting behind.
By Nikki Chwatt