Denim Shorts Review & Comparison

I get a lot of requests for shorts recommendations, so I decided to try on a bunch and do a review and comparison post a la my popular white jeans review post.

Shorts are tricky once you’re past a certain age, but in some regions of the country they’re pretty much a necessity. Even though I love to wear jeans all year round, there are plenty of times during the summer when it’s just too hot, plus I’m not a huge fan of dresses, so shorts are a must for me.

I pretty much live in denim shorts in the summer — I’m sure you’re shocked (#sarcasm) — so I’m focusing on denim styles for this post. I hope to do a follow-up post on other styles of shorts, or I’ll at least include some in my regular Try-On posts.

First, let’s discuss what to look for in a pair of denim shorts. 

Shorts can go really wrong when they don’t fit well, so you may want to start by reading my Fight the Frump: Shorts Edition.

Everyone is built differently so what works for me may not necessarily work for you, but I feel best in shorts with a 3 – 4″ inseam. That said, I tried all different lengths so you can compare.

The hardest thing for me is finding shorts that aren’t too wide in the leg opening. I have wide hips compared to my thin limbs, so often shorts are too wide in the leg, which is a huge frump-alert.

Another thing to consider is the cuff. Some women don’t like cuffed denim shorts because it draws attention to the area of the leg where the cuff sits. I don’t mind this because that’s generally a thinner part of my body, but it’s something to keep in mind.

As with jeans, you definitely want to pay attention to the rear pockets. Pocket placement can make or break a pair of denim shorts just as they can with a pair of jeans — perhaps even more so! I prefer pockets that aren’t too large, and I don’t want them placed too high or too far apart. I’ve only learned this by trying a bunch, taking pictures, and comparing. Again, everyone is different, but this is what works for me.

Finally, distressing. I know, I know. Someone will tell me that anyone who pays money for a pair of shorts or jeans with rips and tears is a slave to fashion. Whatever. I like them. If you don’t like them, don’t wear them. Never fear, I will show a variety of options!

For reference, every pair of shorts I’m wearing in this post is a 29 or size 8 unless otherwise noted.

Denim Shorts Under $100

BlankNYC does a good job with jeans under $100 so I thought I’d try their shorts. Sorry, but those rear shots are always blurry. It’s probably a blessing in disguise — I realize no one really wants to see a head-on shot of my rear view, but it’s necessary when comparing shorts.

These are actually pretty good. I like the fit, and while the leg opening is a little wider than I prefer, I don’t think it looks dreadful. I just can’t say how they’d fit after wearing them for a few hours – if they stretch out, all bets are off.

BlankNYC Boyfriend Denim Shorts // 3″ inseam // $68
also wearing: grey tee // nude sandals

The one thing I don’t like is how those distressed patches are actually woven rather than just threads. I realize that provides some more coverage and prevents them from becoming gaping holes, but I feel like it cheapens the look of the denim, which is otherwise really good for the price point.

High rise shorts are trending so I felt obligated to try some, but I can’t say I’m a fan. Maybe it’s the front-tucked shirt; I would probably like it better out.

Also, I’m not a fan of the rear pocket placement — it’s rather high. That said, I don’t hate these; at least the leg opening isn’t too wide, but I think I can do better.

J.Crew High Rise Denim Short in Brixton Wash // 3 1/2″ uncuffed inseam // $79.50
also wearing: white tee // sneakers

Another high rise pair by J.Crew’s sister brand Madewell yielded similar results, but I like the rear pocket placement better on this Madewell pair, and the extra half inch in the inseam helps too… I guess. I dunno, maybe I can’t see much difference.

At any rate, I decided to keep these. I don’t really need them (see the AG Hailey below) but I wear jean shorts so much that I figured I can use an extra pair, and I like the higher rise sometimes.

Madewell High Rise Cuffed Denim Shorts // 4″ uncuffed inseam // $69.50
also wearing: grey tee // sneakers

These are the Caslon rolled shorts that I see recommended by other fashion bloggers. I can’t say I’m a fan, but I still haven’t gotten the sizing right. These run HUGE. I’m wearing a size 29 in every pair of shorts in this post except this one. These are a 28, and I definitely need a 27.

The rolled hems are kind of thick, but that’s not a deal breaker for me. The length is nice for those who prefer a longer inseam but don’t want Bermuda shorts.

Caslon Rolled Denim Boyfriend Shorts // 4″ inseam // $58
also wearing: grey tee // nude sandals

These Wit & Wisdom shorts are a bit longer than the rest, and they fit the closest to the thigh. That said, there’s still something about them that I don’t really care for. I think it’s the rear pockets – they’re rather large and spaced too far apart, which has a way of making my rear view look even wider than it already is.

Wit & Wisdom Ab-solution Cuffed Denim Shorts // 6″ inseam // $58
also wearing: grey tee // nude sandals

This pair of Gap 5″ shorts yields similar results. I like them okay from the front, but the rear pockets are huge and don’t do much for me.

Gap Washwell Mid Rise 5″ Denim Shorts (similar) // 5″ inseam // $49
also wearing: stripe tee (similar) // nude sandals

These are the Kut from the Kloth Gidget shorts. I had these in white last summer, and I really like this denim wash, plus the size and placement of the rear pockets is really good.

These are a size 28, as opposed to the 29 I’m wearing in most of the other shorts in this post. Sizing down definitely helps with the leg opening issue, but they do seem to be snug through the rear. This brand notoriously stretches out with wear, so I’m hesitant to send them back for the larger size. I think they will fit fine after I break them in a bit.

These are definitely my favorites from the under $100 shorts I tried.

Kut from the Kloth Gidget Shorts // 4″ regular inseam // $69
also wearing: white tee // nude sandals

Denim Shorts Over $100

I realize most people don’t spend 3 digits for shorts, but I do love my premium denim, and I justify the price tag because I pretty much wear the same two pairs of denim shorts over and over all summer long. Also, I only buy them on sale. I always look for last year’s styles on Amazon or Nordstrom Rack, so I usually get them for under $100.

Case in point, I purchased this pair of AG ‘The Hailey’ denim shorts at Amazon for $99.

These were my go-to denim shorts all last summer. This exact wash is discontinued, but you can see all the current Hailey styles at — conveniently, they’re having a 25% off Friends & Family Sale right now. You can also find the Hailey in several different washes on, where prices vary by size.

I like the size and placement of the rear pockets, and I feel like the leg opening looks good from all angles. These are so comfortable too — there’s nothing quite like AG denim for softness and comfort.

AG The Hailey in 10 Years Days Off // 3″ inseam // $99 on sale
also wearing: grey tee // sneakers

I ordered this next pair during Bloomingdale’s Denim Days sale event last month, so I didn’t pay full price, but they were still pretty spendy for shorts that look like they’ve been through a war zone, ha! I just knew the second I saw them that I would love them.

Yes, they’re very distressed, but I like that. I also really like the fit, so they went in my closet, and you can expect to see them every week of my summer What I Wore posts. #fairwarning

I bought them at Bloomingdale’s, but I’m linking them at since they’re 25% off right now.

AG Bryn Denim Shorts // 2.5″ inseam // $168 *cough cough*
also wearing: white tee // sneakers

This next pair is also pricey, but I bought mine at the end of season last summer when they were marked down. I actually had this style of shorts in a smaller size when I was, well… smaller. I kept trying to fit into them last season and I wore them some, but I was uncomfortable so I bought the next size up when they went on sale.

I really like the fit of these, but they are super low-rise. I’m showing you how they look with the front tuck and also with the shirt left out. I think I like it best left out with these. These are slightly shorter than the Kut from the Kloth Gidget pair above, and I like both equally. If you’re looking for the cut-off style, I’d recommend the Gidget simply because the price is so much better.

Citizens Ava Frayed Denim Shorts (also in white) // 3″ inseam // $168
also wearing: white tee // sneakers

These next shorts came in my last Trunk Club, so I tried them on for you. Paige is one of my favorite brands for jeans, but these shorts are a relaxed boyfriend style and I’m not loving them. They’re pretty wide through the thigh, but again, this is me. If you have bigger thighs, you may like these.

I really detest these rear view shots, I’ve gotta tell ya. Here’s some perspective, though. I usually stand with my legs straight so you can really see how they look, but they are so much more flattering with just a little bend in the leg. I guess it’s a good thing most of us don’t stand around with both legs straight and parallel.

And yes, that’s a big distress mark on the back butt cheek — it’s not a tag or anything. So yeah, not a big fan of these.

Paige Parker Denim Boyfriend Shorts // 4 1/2″ inseam // $169
also wearing: white tee // sneakers

Finally, a longer pair of AG. I apologize that I don’t have any Bermuda length shorts in the under $100 range to show you. I feel like denim Bermudas are less aging than Bermudas in a chino material, and they seem to be trending lately, so it’s something to consider if you’re not a fan of showing your thighs.

These are a size 28, which is what I normally wear in AG jeans, although I sized up to a 29 in the Bryn shorts, since I generally size up in shorts — especially the shorter ones. Conversely, longer shorts really look bad if they’re too big in the thigh area, so I took a chance with the smaller size, and I like how these fit.

Like the Kut from the Kloth pair, they look snug now, but after an hour of wear they will settle in and look more relaxed. AG jeans don’t bag out, but they do loosen up and mold to your body in a flattering way, and I expect these shorts to do the same.

I’m tempted to keep these since I don’t have any longer shorts right now. Maybe I should return the Bryn and keep these…

AG Nikki Cutoff Denim Shorts // 9″ inseam // $168
also wearing: tie front top (similar) // nude sandals

White Shorts

I tried a couple pairs of white shorts, so I thought I’d tack them on here at the end. These are J.Crew but a different style than the blue ones above. They look pretty good to me except that they kind of wrinkle through the rear end. Not sure what’s up with that.

J.Crew Denim Short in White // 4″ inseam // $69.50
also wearing: stripe tee (similar) // sneakers

I find this side by side (or top by bottom) comparison interesting. Two pairs of cuffed white denim shorts with approximately the same inseam length, and the ones below are far more flattering, in my opinion.

The ones above are fine, but when you see them next to (or above) the AG pair, there’s no question which pair I’m keeping and which pair is going back. It’s really all about the pockets and that leg opening!

AG Hailey in White Restored // 3″ inseam
also wearing: stripe tee (similar) // sneakers

I hope this was helpful. I wanted to include some from Loft and White House Black Market, but I haven’t had a chance to try them. I tried to find them in store, and they weren’t carrying them yet. Talbots is also worth checking; I know some of you like shopping there.

Do you have a favorite pair of denim shorts? Share them in the comments!

Don’t miss a post!

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. Don’t miss it!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!