Last year I did a round up of three denim shorts and ya’ll loved it. But this year I decided to go harder, as I do. I tried on 11 different pairs and I’m breaking them down for you below! I’ll be honest, there are a lot of high rise because that’s just what’s in store right now but not all high-rise are created equal so be sure to read the descriptions below each pair. Also I included a crop and a booty shot for each. Bonus points if you can spot the one’s where I have a wedgie lol.

PS: A lot of these options are included in the Shopbop sale event, I’ve listed them from multiple retailers below but wanted you to check them at Shopbop first for the discount! 

Just as a reference, I am 5’9″ and about a size 6 or 28 in denim. Do what you will with this information.


Best Everyday Pair

high rise
size up for a relaxed fit
soft vintage feel

I would say if you’re looking for a less high rise pair, give these a shot. They’re definitely a high rise (11.5″ rise) but they fit relaxed so they don’t feel super confined like a typical high rise. I was actually surprised to find that they had such a long rise because I considered these mid-rise. But I’ve got a freaky long top so good luck finding my belly button.

I wear the 29 in the Parker vintage shorts. I size up in these (but you don’t have to!) because I like them slouchy. I tried the 28 of this pair but they were way too short for me. The waist fit but they were a bit too cheeky for my personal preference. If you want a slouchier fit, then size up one!

Find them at Shopbop.

Find them at Nordstrom.

Find them at Verishop.

Find them at Revolve.

Best Relaxed Fit

relaxed fit
true to size
relaxed thighs
4.25″ inseam

If you’ve tried the Parker vintage shorts but they were a little too short for your liking, try the Reese fit! They fit a little bit more fitted at the hips / waist and are a true high rise fit (they hold everything in!) I like the longer length and the thighs seem to be more relaxed on this pair compared to the Parker.

I am in the 28 of the shorts here, they fit true to size. I find that Agolde does relax as you wear them. I wouldn’t say a whole size but they definitely get a nice worn in feel to them, especially if you don’t wash them a ton.

Find them at Bloomingdales.

Find them at Shopbop.

Find them at Anthropologie.

Best White Denim Short

under $40
true to size
distressed hem

I gave this pair a shot in a try on a few weeks ago and really loved them. Unfortunately I listened to the reviews that said to size up at least 2 sizes and I got a 30. No ma’am. These shorts have a generous fit AND lots of stretch. Think a stretchy denim fabric for these. The only reason I would suggest sizing up is for length because they are pretty short. I settled on a 29 for the length and leg openings, but the waist is slightly loose.

A nice quality, as well. They aren’t sheer which is a blessing for any white denim. Also this pair is a great mid-rise fit, as well! Click through below for more color options other than white if you are looking for a mid-rise option.

Find them at Amazon.

Best Distressed

high rise
true to size

This is a pair I bought two summers ago and LOVED so much that I bought again this year. (I’ve lost some weight so I needed to size down, otherwise the other pair is still in great shape. This pair washes well and wears well. The distressing loosens but stays intact.) This pair is definitely risqué, at least for me. The distressing is quite dramatic but their so unique I just love them. The denim that’s not distressed is a thicker denim that molds to your shape and becomes more worn in as you wear it. They really age well, which is a huge plus.

The fit is true to size! They are high waisted, they hit me right below my belly button. I am in the 6 here.

Find them at Shopbop here.

Find them at Nordstrom here.

Find them at Good American here.

Best Budget Find

under $40
size up one for a truer fit
slightly distressed

These are the Old Navy High Waisted O.G. Shorts and I was super surprised by how well they it. I find denim shorts to be a hit or a miss at Old Navy but these slid on like a glove. They’re a great fit, I sized up to an 8 and they fit perfectly. The inseam is a 3″ and it doesn’t seem too short and it covers the booty, which is so nice. They are lightly distressed but no major holes! The denim seems like it will soften with washing and wearing as well.

Find them from Old Navy here.

Best Mom Jean Shorts

extreme high rise
nice booty coverage
vintage look
always has snacks in her purse

If you are here for the 90s revival, then this is the pair for you. Mom jean but make it shorts. This is your classic mom jean cut — slimmer waist, high rise and wider at the legs. This cut rounds out your hips and booty as well. I really like this pair because they are comfortable, if you like a high rise and let me tell you — the rise on these is a real overachiever. I mean look at that zipper, they had to borrow this one from a sleeping bag it’s so long.

In other words, if you don’t love an overdramatic high rise, please do not apply. These are the highest rise I’ve ever put on my body and I love them. I am in the 28, I would say true to size and they will stretch with wear! The length is a bit shorter on the sides but I felt pretty comfortable with the booty coverage. True to Madewell denim sizing.

Find them from Madewell here. 

Best High Rise

high rise
nice inseam
under $100

I should say the best (not up to your boobies) high rise. If you want that, see the aforementioned mom jeans pair.

For my high rise loving friends, I love this pair from J.Crew. They’re a great price, I love the mid-blue hue and the high rise holds everything in. I slipped them on and it just felt like a pair that I’d had for years. They fit perfectly right out of the bag. They do have stretch in them, so they are more fitted in the thighs and hips. I don’t anticipate this pair stretching out much with wear. I am in the 28 here, I’d suggest true to size!

I also feel like these are just a classic look for denim shorts. They aren’t too fitted, they aren’t too distressed and the length is just right.

Find them from J.Crew here.

Best Option for Thick Thighs

high rise
generous fit
frayed hem
relaxed thighs

The number one question I get when I post shorts on IG is: ‘will they work for thicker thighs??’ I completely understand this question, as I’m somewhere in between. I have more athletic thighs, so when shorts are super tight on me it throws my whole vibe off, you know? If you too hate thigh sticking shorts, than this is the pair from you. This pair is from LOFT and it’s the a nice relaxed fit in the waist and the thighs. It’s the kind of pair of shorts that yo want to wear all summer long. The fit is generous, but I am in the 6, so I’m gonna say true to size. If you are in between sizes, you can size down one or just expect a relaxed fit.

Find he Loft shorts here.

Best Classic Cutoff

true to size
high rise
shorter inseam

It’s a toss up between Madewell and Agolde denim for my favorite brand of shorts. Both wash and wear so well and the fits are always reliable. This pair from Madewell is probably the shortest pair that I have (so scandalous) so defiantly note the inseam and length here. They do fit relaxed but they are true to size, I am in the 28. Because they are 100% cotton, they do not have stretch, however so they will stretch out with wear and wash back to their size.

Find them from Madewell here.

Find them from Nordstrom here.

Best Mid-Length Pair

Last year the Bermuda short trend was trying to peek her head around the door to see if it was safe to come out again. We shut the door on her face real quick. HOWEVER, I do respect a longer length short. Not all the way to my knees because that’s a lot of fabric to not be a whole jean, but mid-thigh I can do. I was pleasantly surprised by this pair from Levi’s (I decided to go with a tried and true brand I like for this trend.) They fit exactly like 501s if you’re familiar with that fit — a structured denim, high rise and flattened butt, if we are being honest. So keep that in mind for this pair of shorts.

For the fit, I sized up to a 29. I’ve learned my lesson with Levi’s shorts and the lesson? SIZE UP. They fit tighter than the jeans in the waist, or at least for me they do.

Find them from Shopbop here.

Best Unpopular Opinion

paperbag waist
high waist
relaxed fit
not here to make friends

I saved this pair for last because I just know you’re gonna hate them. *nervous laugh* We can split the population into two uneven groups — those who like a paperbag waist and those who immediately want to throw it in the trash. I’m obviously a fan even though I don’t have much of a defined waist so a paperbag waist really is like putting a rubber band around an apple. But they are comfortable and I am feeling this 90s mom at summer camp vibe. Get me a visor and a banana clip, I’m going places.

I am in the medium but they are a very generous fit. I could easily size down to a small in these, as they’re very generous in the waist. I would say if you’re an 8/10, the medium will fit great! I mean, as great as a paperbag waist is gonna fit. LOL. Why do I love this trend? I’ll never know. The heart wants what the heart wants.

Find them here at Nordstrom.

Find them here at Shopbop.



Shop the Outfit

Fit Details

I am in the medium of the tee! True to size. The slides run slightly wide, but I’m in my typical size 10. You could size down a half size if in between sizes.

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