All of the Most Stylish and Flattering Denim Shorts to Shop for Summer

Finding the perfect pair of jean shorts can be daunting, but it's not impossible.

Denim shorts are a summer wardrobe staple. Julia Cherruault for Observer

While summer style trends come and go, denim shorts remain a classic warm weather staple of peak Americana fashion. Shopping for a flattering pair of jeans shorts can be daunting, to say the least, but it’s not impossible, especially when you have a little guidance to help sift through the good, the bad and the very, very ugly.

I thought I found the holy grail of denim shorts while shopping in one of my go-to stores, also known as my mother’s closet, several years ago. In my biased point of view, these incredibly flattering Levi’s were the best cut-offs ever made, thanks to the fashionably frayed (yet not sloppy) hem, loose leg and just-high-enough waist. They were a very specific shade of light wash denim that I didn’t think existed, but much to my dismay, these shorts disappeared approximately three years ago.

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I’d hoped to simply order a fresh pair online, or, at most, actually go into the Levi’s store (IRL retail!) and rebuy the very same style. Alas, my mother revealed that she obtained these magical cut-offs around 1977. Yes, seriously. I also learned that this particular style doesn’t actually exist, as she cut them herself, which explained why my quick replacement strategy didn’t go as smoothly as I’d hoped.

Sadly, while I’ve yet to find an exact replica of my long-lost vintage Levi’s, my extensive search did lead me to plenty of stylish denim shorts (including a few pairs of Levi’s) that are both flattering and fashionable—as long as they followed a few rules.

So, what are my requirements when it comes to the best jean shorts? There are a *lot* of options out there, so always opt for what you feel most comfortable wearing. I personally prefer a loose leg, high waist and slightly faded wash when it comes to cut-offs, and pass on anything that’s cuffed or hugs my thighs too much, because no one enjoys having to constantly tug down on shorts that are clinging to your legs in the sticky summer heat.

It’s important to choose what works for you, but as a general rule, I recommend almost always sizing up in jean shorts; it’ll keep you from looking like you’re wearing glorified denim underwear, because while some people can pull off the Daisy Duke vibe, I’m very much not one of them.

Summer is just around the corner, so now’s the time to add a classic pair of denim shorts to your closet. Below, take a look at the flattering, comfy and stylish jean shorts to complete your essential warm weather wardrobe.


DL1961 Cleo High-Rise Shorts in Lapis Distressed

Everyone has a different definition of the perfect shorts, but these check *all* my requirements. They’re high-waisted, loose at the raw hem and are just slightly longer on the inner thigh than outer thigh, for a leg-lengthening illusion. $139, DL1961.


Levi’s Ribcage Women’s Denim Shorts

No, these aren’t the aforementioned vintage Levi’s cut-offs, but they are a cute and flattering alternative! These have an ultra-high waist and gently frayed, angled hem, and are thus far the closest I’ve come to replacing my beloved 1970s-era pair. As I mentioned, I prefer a looser fit, so definitely recommend sizing up in this particular pair. $79.50, Levi’s.

J. Crew.

J. Crew High-Rise Denim Short in Tea Time

These cut-offs already have the perfect lived-in look, and they fit so well. They also have just enough stretch, so they’re ultra comfy. $79.50, J. Crew.

Joe’s Jeans.

Joe’s Jeans Emmy Short

If you just want to go all out with an acid wash, try this high-waisted cut-off style, for a 1980s vibe. $128, Joe’s Jeans.


Etica Sydney High Rise Short in Granite Creek

It’s always important to keep sustainability in mind when shopping, and these washed-grey shorts are made of eco-friendly denim. They’re a cute alternative to traditional blue jean, and are great for those who want a high-rise waist that doesn’t go too far up on your stomach. $128, Etica


Sundry Hearts Slouchy Shorts

If you’re looking for a more demure style, consider this medium-wash, straight-leg silhouette. These are on the looser side, with adorable heart stitching on the back. $168, Sundry.


Abrand Jeans A Venice Short Daisy Blue

These light stonewash shorts feature a flattering high-waist and subtly flared hem, and they also have a bit more stretch to them than many of the stiff cotton fabrications out there. $69.82, Abrand Jeans


L’Agence Audrey Short

If you’re ready to make a serious splurge on your next pair of denim shorts, try these distressed mid-rise cut-offs. They’re ideal for those that aren’t feeling the high-waisted trend. $240, L’Agence.

Nasty Gal.

Nasty Gal High Waisted Denim Raw Hem Mom Shorts

Is there such thing as an LBD of denim shorts? Well, these might be them. $27, Nasty Gal.


Frame Le Grand Garcon Short Raw Fray Bathe

These are definitely on the more relaxed end of the already-casual denim shorts spectrum, thanks to the ultra-distressed hem, and the style is also ultra-lightweight, which is very much appreciated during the humid summer months in the not-so-distance future. These are also sustainably made. $178, Frame.

Kut from the Kloth.

Kut from the Kloth Gidget Fray Hem Short

Dipping your toes into white denim short territory? Try this stretchy mid-rise pair, with a neatly frayed hem. $69, Kut from the Kloth.


Levi’s High Loose Denim Shorts

You didn’t think we’d stop at one pair of Levi’s, did you? These aptly named “High Loose” denim shorts are one of the more universally flattering styles out there, and if you want more of a vintage-y frayed look, just cut at the hem like a teeny tiny bit—proceed with caution, though! $79.50, Levi’s.

Veronica Beard.

Veronica Beard Jean Jaylen Pleated Shorts

These aren’t exactly traditional, but the girly silhouette of these high-waisted, cinched pleated shorts is just so chic. $230, Net-a-Porter.


Wrangler Reworked Short in Light Stone

If you’re not feeling too confident in your fabric-cutting skills, but *really* want to achieve the cut-off aesthetic, try these Wrangler shorts, as they’re specifically designed to mimic the look of worn-in denim cut-offs. $69, Wrangler.


Agolde Criss Cross Organic Denim Shorts

There’s a reason people go crazy for Agolde’s flattering denim, and these shorts are no different. They’re also a fun alternative when you’re seeking a longer style. $170, Net-a-Porter.

All of the Most Stylish and Flattering Denim Shorts to Shop for Summer