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.
The Top 5 Relaxed Denim Shorts
— Best for the Workplace: AGOLDE Dame Shorts ($178)
— Best for Summer Weekends: FRAME Le Easy Denim Shorts ($94)
— Best Vacation Style: CITIZENS OF HUMANITY Brynn Denim Shorts ($240)
— Best for Styling with a Blazer: NILI LOTAN Russel Denim Shorts ($350)
— Best Affordable Option: H&M Denim Shorts ($25)
These one of J.Crew's top-rated shorts styles, and I can see why.
Washes: 1 wash
Size Ranges: 23-37
I always look for how roomy shorts are in the leg, and this Mango pair looks like the perfect relaxed fit.
Washes: 3 washes
Size Ranges: 0-14
I love when a good shopping find comes with an even better outfit idea.
Washes: 4 washes
Size Ranges: 25-32
Shocking no one, Levi's is behind one of the summer's most in-demand denim shorts.
Washes: 1 wash
Size Ranges: 24-32
I love how these hit at a cool mid-length that's elevated and ultra-wearable.
Washes: 1 wash
Size Ranges: 23-34
It's all in the name: These shorts couldn't be any easier to wear.
Washes: 1 wash
Size Ranges: 23-32
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.
Washes: 2 washes
Size Ranges: 23-33
These have everything I'm looking for in a pair right now—10/10. No notes.
Washes: 1 wash
Size Ranges: 23-34
I love how these sit lower on the hips for an even more relaxed look.
Washes: 1 wash
Size Ranges: 24-31
You'll wear these so frequently the cost per wear will be virtually nonexistent.
Washes: 5 washes
Size Ranges: 0-18
"Editor" is right there in the name, so you know these shorts are good.
Washes: 1 wash
Size Ranges: 2-12
This darker wash is so elevated.
Washes: 3 washes
Size Ranges: 23-32
Bermuda shorts are back, baby.
Washes: 1 wash
Size Ranges: 2-12
Madewell has perfected its '90s jeans, so it should come as no surprise that the brand has also mastered relaxed denim shorts.
Washes: 3 washes
Size Ranges: 23-33
The perfect way to show off all your summer sandals.
Washes: 1 wash
Size Ranges: 23-32
I'm copying this look and wearing my Bermuda shorts with pretty ballet flats.
Washes: 1 wash
Size Ranges: 23-32
These are a great stepping stone between regular denim shorts and relaxed fits.
Washes: 2 washes
Size Ranges: 24-33
Mother never disappoints when it comes to denim.
Washes: 1 wash
Size Ranges: 24-32
The latest iteration on sweatpant jeans — cozy yet baggy without being unrefined.
Washes: 3 washes
Size Ranges: XXS-XL
The combination of this silhouette and wash is perfection to me.
Washes: 2 washes
Size Ranges: 23-34
I love this subtly frayed hem.
Washes: 1 wash
Size Ranges: 23-33
These top-rated shorts come in six staple washes.
Washes: 6 washes
Size Ranges: 23-37
I love how these relaxed shorts are styled with a button-down for a hint of polish.
Washes: 1 wash
Size Ranges: 26-32
Paige has some of the softest denim I've tried.
Washes: 10 washes
Size Ranges: 23-34
This mid-length is great when you're not in the mood for revealing short-shorts.
Washes: 8 washes
Size Ranges: 23-32
FAQs
What is relaxed denim?
Relaxed denim refers to styles that have a looser, more comfortable fit compared to skinny or slim styles. Typically, they have a straight or slightly tapered leg and offer extra room for movement, giving off an effortlessly cool, laid-back look. I personally love making any style feeling relaxed by going up a size.
Why trust Who What Wear?
Who What Wear is a trusted source because it's built by experienced editors who have experience in expert-backed insights, trend forecasting, and product recommendations that are both stylish and wearable. Oh, and I think each and every one of us has a really great pair of relaxed denim shorts on hand.
This post was published at an earlier date and has since been updated.
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