18 Denim Shorts That Are Always Cool, Never Basic

Denim shorts, much like the crop tops or tight dresses of the world, tend to dance on that fine line between rad and basic (yes, in the negative sense of the word). It's all too easy to settle for the mass-fashion end of the spectrum when it comes to these types of trends (you know those millions of "meh" options we're talking about). But if you're looking to edge toward the side of cool, you really just have to know where to shop.

While we all have that pair of cutoff denim shorts we automatically reach for on a too-hot weekend, you won't regret having an alternative on hand that's a little more of a conversation starter. Wouldn't you rather show up to a party and stand out? Click on to shop some next-level denim, and leave those denim diaper shorts in the back of your drawer in exchange for one of the offbeat picks ahead.

1 of 18
A pinstriped pattern and slightly oversized fit are no-brainer ways to make your denim shorts feel fresh.

Zara Striped Denim Shorts, $35.90, available at Zara.
2 of 18
Try a paper-bag waist that you can show off if you're a diehard T-shirt tucker.

C/meo Collective Floating High Short, $120, available at Need Supply Co.
3 of 18
How about ditching the usual shorts altogether for a suspender skort?

W Concept Wixson Overall Denim, $89, available at W Concept.
4 of 18
Make grandma proud with some detailed embroidery.

Topshop Moto Embroidered Mom Short, $60, available at Topshop.
5 of 18
Get a model-off-duty vibe with a high-waisted, washed black pair that's "airport style"-ready.

Levi's® | Re/Done The Black High Rise Short
Black High-Rise Short, $177, available at Re/Done.
6 of 18
A retro-looking pair for the mornings when you wake up feeling like you were born in the wrong decade.

Samantha Pleet Spectrum Shorts, $145, available at Garmentory.
7 of 18
Elastic waistbands mean you can comfortably eat as much as you want at brunch.

Chloé Frayed Denim Shorts, $550, available at Net-A-Porter.
8 of 18
Get two looks in one: One hue in front and another wash on the back.

NastyGal After Party Vintage Levi's 501 Cutoff Shorts, $68, available at NastyGal.
9 of 18
Who said layering's irrelevant in the summertime?

R13 Double-Layer Short in Bristol Blue, $345 $205, available at R13.
10 of 18
The higher-waisted the better.

Pixie Market Waist Belt Tie Denim Shorts, $78, available at Pixie Market.
11 of 18
Another way to make the Bermuda-shorts trend all your own.

AALTO Denim Shorts with Front Pleats, $280, available at Opening Ceremony.
12 of 18
See? Denim can do colorblocking, too.

See by Chloé Button Fly Shorts, $275, available at The Dreslyn.
13 of 18
It's all in the (seam) details.

Lemaire Shorts, $445 $311.50, available at The Line.
14 of 18
Sequins are never off limits.

Ashish Sequined Destroyed Denim Shorts, $1,134 $680.40, available at Farfetch.
15 of 18
A button fly will have you looking fly 'til you die.

Stylenanda Button Fly Cutoff Shorts, $41, available at Stylenanda.
16 of 18
Patchwork doesn't have to look full-on Dolly Parton.

Assembly Denim Patchwork Short, $288, available at Assembly.
17 of 18
Your all-black outfits deserve an artful upgrade.

Mango Embroidered Cotton Shorts, $69.99, available at Mango.
18 of 18
Not everything in your closet has to be so symmetrical.

Bless SMLXL Shorts, $427, available at Creatures of Comfort.

More from Shopping


R29 Original Series