WTF, Denim Shorts!?

the problem with denim shorts | The Stripe
jacket // top // shorts // bag // sandals

I’d really like to write an open letter to nearly every brand who makes denim shorts and just ask them something that’s been on my mind for a while now. “Whyyyyyyyyy must you make all of your denim cut-off shorts look like a teensy-tiny denim diaper?!” I’m a woman in my mid thirties who is in decent shape and not a total prude I cannot find a good pair of denim shorts (save for this pair) to save my life. Last year I placed an order with Shopbop (I ordered like, eight or nine pairs) and they were all terrible. They are all either a) too tight, b) too short, c) cut so that the pockets hang out of the seams (just can’t do it, Britney traumatized me), or d) at the other end of the spectrum: too frumpy… like a Bermuda short.

I’m not alone in this. All of my girlfriends have the exact same issue. All of them. One friend was at Madewell a few weeks ago before a vacation and she couldn’t even find an appropriate pair of denim shorts there. No shade to Madewell! It’s the best for cute, classic clothes – one of my favorite places to shop and… not exactly scandalous. UGH. Come on brands! The Rag & Bone boyfriend short is literally the only acceptable denim short I’ve found. It’s ripped so it’s still cool, it’s an acceptable length, and it’s not too tight. They’re not perfect though – I’d love to find something a little less tattered and they do stretch out. I also have two pairs from Joe’s Jeans (these and these) but they are a little short… better for the beach!

Readers, I’m dying to know… do you have a favorite pair of (not too short, not too tight) denim shorts? And if so, where did you find them!? I’d love to find a pair like the ones I’m wearing that’s not so… tattered. Maybe this is my next business idea… designing a line of denim shorts for women who want something in between totally scandalous and totally frumpy.

Outfit Details: Madewell Fleet Jacket // Rebecca Taylor Top // Rag & Bone Shorts (mine are a few years old but this is the new version – more options here and here) // J.Crew Corsica Espadrilles // Cult Gaia Bag (I have the large one) // Hart Hagerty Tassel Earrings // Celine Sunglasses

the problem with denim shorts | The Stripe the problem with denim shorts | The Stripe the problem with denim shorts | The Stripe the problem with denim shorts | The Stripe the problem with denim shorts | The Stripe

photography by Lydia Hudgens.

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  1. Omg, I agree! I can’t seem to find denim shorts these days which aren’t triangular in shape, like underwear is. I mean, they’re shorts, not underwear…

    Charmaine Ng | Architecture & Lifestyle Blog

  2. Stella C. says 5.19.17

    I completely agree with your denim short assessment!

    They’re literally THE WORST. Last summer, I eventually called it quits on my hunt and took my shears to an older pair of boyfriend jeans (I believe they were JOES) and cut across the legs about 3 1/2 inches out from the crotch. You cut at a slight angle so the shorts end up a bit longer in the crotch area, and shorter on the sides. The 3 1/2 inches were perfect for the inevitable fraying that happens, or a slight turn-up cuff. Best decision ever made and people always stop to ask me where I got my shorts from!
    Have a great weekend!

    xo Stella

  3. Kelsey says 5.19.17

    Oh please post again when you find more shorts that you like!! I feel like every summer I am in the same predicament! I am not above a short pair for the beach, or maybe even a day date with some cute flats. But when I want to go to the park with my kids….no one needs to see that much of mommy!

  4. Marta says 5.19.17

    I have the same problem but it’s with shorts in general, not just denim ones. It’s hard to find pretty AND comfortable shorts. I feel like they’re either too short (don’t feel confident enough to wear them) or too “posh grandma-ish”. But those are gorgeous and they look amazing on you. And that top is super cute as well.

  5. Maggie says 5.19.17


    I found a of 7s on Zappos that were just what I was looking for! (Relaxed mid roll short) moderate distressing and a 4 inch inseam. The denim is super soft! I’m usually between a 27/28 and went with the 28 for a more relaxed fit!

  6. Cathleen says 5.19.17

    Very cute outfit. I agree on the shorts being ridiculous anymore. I just don’t wear them. I’ll usually find a jean skirt.

  7. Allison says 5.19.17

    I buy the boyfriend shorts at Old Navy every summer! I always size up because I have a decent behind and need the bigger size for them to be “boyfriend” fit. I’ve recently started getting rid of my older shorts because I agrees with you! Two inch inseams just can’t happen anymore!

    • Emily Rose says 5.21.17

      Yes! I was just about to suggest the same thing. Looser fit, higher rise and acceptable length! Not to mention great price!

    • grace at the stripe says 5.22.17

      That’s such a good idea… thanks Allison! xo

  8. Briana says 5.19.17

    Totally agree with you here. I actually ended up taking a pair of my J.Crew boyfriend jeans (since they’re a little bigger in the leg) and cut them into shorts so that I could control the length. It’s worked pretty well for me, although I’d still like to find some that aren’t distressed like you’re saying.

    Briana |

    • grace at the stripe says 5.22.17

      That’s really smart. Thinking I may do the same with a pair of baggier jeans I have.

  9. Abby says 5.19.17

    This made me crack up – I have the same problem too! I actually think Gap makes really good denim shorts.

    • grace at the stripe says 5.22.17

      A lot of suggestions to go to GAP and Loft – I’m going to have to pay both a visit!

  10. Brittany says 5.19.17

    okay, i am kind of a jorts (sorry…) fanatic and wear them daily. one of my favorite spots is the vintage ones from

    I also posted some of my faves in this post:

    xo, brittany
    weekend links + steals on my blog today!

  11. Molly says 5.19.17

    My favorite are j.crew so far – the ones I have arent tattered, arent too tight (but maybe a little too loose), and not too short! They are also a darker denim so they look a little more “respectable” maybe? haha.

  12. Brittany Cerminara says 5.19.17

    Completely agree! I finally had success with J Crew factory.

    • carrie says 5.21.17

      Me too – J Crew Factory were the only acceptable ones for me as well!

    • grace at the stripe says 5.22.17

      Good to know! I forgot, but I got a great white pair from J.Crew factory last year.

  13. Olivia Broderick says 5.19.17

    I have some from Gap that aren’t too bad. I know Gap’s quality has gone down in recent years, but I’ve always found their denim to still be pretty good.

    Best of luck!

    • grace at the stripe says 5.22.17

      I’m going to have to take a peek at GAP – I used to shop there constantly but kinda stopped, recently… may have to revisit!

  14. Jenny Kepler says 5.19.17

    I feel your pain! I found the BEST pair of denim shorts from LOFT this year — long enough, cuffed and still cute (and not tight)!

  15. Rachel says 5.19.17

    I’ve been buying jean shorts lately at LOFT. They have a good selection of denim and non denim shots.

    • grace at the stripe says 5.22.17

      A lot of people have said go to LOFT – I’m going to have to take a look! xo

  16. Natali says 5.19.17

    While I do love my regular jeans and could live in them whole year around, I’m not into shorts for some reason. I do love to wear skirts and dresses in Spring and Summer, but rarely ever put on shorts. When I do put them on, it’s usually when I’m heading to the beach.
    You’re looking lovely as always!

  17. Ha! I love this! I totally agree, denim shorts are hard to find a good pair of!

    I hope you’re having a lovely day!

  18. Erica says 5.19.17

    I am so glad you made this comment! I have recently ordered 10+ pairs of denim shorts searching for a good replacement for my Joe’s that are about to die. I also wanted a high waist (2 kids in 2 years). They are next to impossible to find. I thought I found a good pair at Zara. Only after a few wears did I decide they were too short for this 40-year old mama. For now I’m wearing them, but I feel a little inappropriate every time I do!

  19. Emily says 5.19.17

    I completely agree and pretty much despise cutoffs that always lead to wedgies 🙂 However, I got these about a month ago and so far absolutely love them – seem to be a nice happy medium!

  20. Katie says 5.19.17

    I completely agree with this sentiment! I don’t get why denim diapers are so popular, especially the ones that are cut so short, but are also baggy somehow?? (i.e. One Teaspoon brand). I basically didn’t wear any shorts last summer because I couldn’t find any styles I liked/didn’t make me feel too exposed, too tight, or look young like a 12 yr old somehow. This year, I made it my mission to find cute shorts. Enter Vince. They are nailing it this year! Now, they don’t offer the classic denim short you’re looking for, but I thought I’d post anyway because they are doing great with cotton shorts. I bought the Utility Short in White, and they are beautifully high-waisted, yet stretchy so they are comfortable to move around in (I wanted to buy the Jesse Kamm shorts because I love the high-rise, but omg they are so uncomfortable and so restrictive around the waist, I have no idea how anyone wears those pants/shorts can stand it), and the length of the Vince shorts is just enough to feel covered but not at all frumpy. They basically make me feel like a chic lady on a yacht. Who doesn’t want to feel like a chic lady on a yacht! 🙂 (These ones: They do have a couple variations on this style as well, worth checking out!

    • grace at the stripe says 5.22.17

      Ooooh I will have to take a peek. Vince is probably the designer I buy most of… such good basics!

  21. KimR says 5.19.17

    To get the denim shorts I wanted, I had to cut off a pair of distressed jeans I already owned. I already knew I liked the fit of the jeans, and cutting them off myself let me control the length. Maybe not the perfect solution, but it gave me the jeans shorts I wanted and they were true “cut offs.”

  22. Sara Chesley says 5.19.17

    You want jeans with a minimum of a four inch inseam, I am 5’7 so I like a 5 inch inseam, Loft and Jcrew ftw!!!

  23. Lauren says 5.19.17

    I did the same thing last summer where I ordered a ton of jean shorts from Shopbop and they were all terrible. I have one pair of vintage Levi jean shorts that work, but otherwise it has been impossible. I’ll check out the R&B ones you linked – they look super cute on you!

  24. Meghan says 5.19.17

    Ugh, totally with you on this. I have never thought itty bitty jorts were comfortable (or flattering!) but it’s so hard to find a non-geriatric longer pair!

    Have you tried DL1961? They have inseams ranging from 3-5.75″. AG has a pair called the Hailey that’s 3.5″ inseam, and their friends and family deal is on right now (25% off with code FF25). As a bonus, both companies use more eco-friendly processes than your average denim shop 🙂

  25. joanna says 5.19.17

    i’ve had decent luck with gap and old navy of all places!!

  26. aurelia says 5.19.17

    Hi grace! The only denim shorts that I can buy are pilcro brand at anthropologie. They are AMAZING and a great price point. Def check them out, they have lots of fun colors as well!! ❤️

  27. Sara says 5.19.17

    I didn’t wear shorts for YEARS because of this exact issue. You’re going to laugh, but honestly, my favorite pair of shorts I’ve gotten recently are from Target. The Mossimo or Lee brands I’ve found are the best. What’s even better is that when you go on the website, you can actually filter by inseam. Super helpful. Here’s a link with inseams from 4″ – 6″ for Lee and Mossimo:

    Also, Uniqlo has a decent pair of boyfriend denim shorts:

    • grace at the stripe says 5.22.17

      Wow – these look really great (and such good deals) – thank you for suggesting!

  28. Caitlin says 5.19.17

    Ugh I could not agree more. It is so frustrating! Your shorts are absolutely perfect though, I should try out a pair!
    xo, Caitlin

    • grace at the stripe says 5.22.17

      Thanks, Caitlin! I love mine… there are lots of great suggestions here in the comments too!

  29. Dana says 5.19.17

    I had the same quest this spring, and wound up loving a pair from a random Nordstrom brand, Kut from the Kloth- finally, jeans shorts with an inseam for a normal person! They have both distressed and classsic versions, and you can’t beat the $60 price- total win.

    • grace at the stripe says 5.22.17

      I am going to check those out – Nordstrom’s random little brands can be really great (and affordable)

  30. Tracy says 5.19.17

    Old NAvy

  31. Victoria says 5.19.17

    AGREE. I bought my first pair of denim shorts in YEARS last fall when we were going to Kauai. Living in SF my shorts game was non-existent and when we were in NY I think I just wore dresses all the time. Anyway, all the denim shorts were HORRIBLE except for one single pair from Joe’s. The pair I got from them (also seriously discounted since I shopped ’em in like October) have no fraying at all. They’re actually just a hair too long, but meant to be worn with the cuff rolled up a little. I was surprised how much I liked them — they are fitted enough in the back, but not too tight in the leg, and just long enough. No diaper-ing either. These are the ones (though sold out now: I dunno, they work and I do like them, but I still prefer these linen tie shorts I got during the same pre-vacay shopping spree ( ; hope they come back this year!). Denim shorts, even when you find good ones, are kinda just the worst.

  32. Monica says 5.19.17

    The struggle is SO real…I’ve seen some from J.Crew that looked cute, but haven’t actually tried them (that’s on me)…for now, I’m just wearing the pair I bought 5 years ago. They’re Paiges–purchased for like $35 at Nordstrom Rack– and were actually this awkwardly long length with frayed hems, so I folded up the hem and ironed them down and wear them as slightly cuffed ones now. It should NOT be this hard, ugh! Please design a line 🙂

  33. Latisha says 5.19.17

    I’m soooo glad this was addressed!! It’s such a problem! I don’t have a single pair of shorts that fit just right. Girl, I started sewing my own shorts!

  34. Lainey Lofland says 5.19.17

    Gap has always had some really cute ones! 😉

  35. Leslie says 5.19.17

    I always buy a pair of jeans one size too big and cut them off. They’re flattering and you can control the length.

  36. emily lunstroth says 5.19.17

    I AM THE SAME WAY!! Well i am not not a prude because i don’t love my legs but I just want to love myself in jean shorts. I ordered a CE pair and the fray on them looked like I was in HS!! They are being sent back tomorrow….I think I just need to bite the bullet and get the R&B ones because I love them on everyone I see!

    • grace at the stripe says 5.22.17

      They’re really the best. Though the Current Elliot ones another reader mentioned look great too… a little less destroyed.

  37. Brooke Butler says 5.19.17

    I completely agree! It’s so hard to find a good pair of denim shorts. I run into the same problem with swimsuit bottoms!

    xo, brooke

  38. Lisa says 5.19.17

    I am 100% behind this business idea. Denim shorts are the worst!

  39. Mere says 5.19.17

    Totally feel your pain. I live in denim shorts in the summer. In fact, last year I bought the very pair you’re wearing in these pics b/c I saw them on you and thought they looked perfect! A good alternative to the Rag and Bones… Current Elliott’s The Boyfriend in Super Loved Destroy (for some distress but not as much as our Rag and Bones) or The Boyfriend in Loved for a no rip classic look.

    Good luck!

    • grace at the stripe says 5.22.17

      Thanks so much for the suggestion – these both look great!!! Like the Rag & Bone but less destroyed!

  40. Mia says 5.19.17

    Girl, I have this issue every summer – and this summer being pregnant is not making it any easier! The only the worse than the regular jean shorts currently on the market are maternity jean shorts!!

  41. Kate says 5.19.17

    I have a pair of the more classic J. Crew ones (non ripped, came cuffed), and recently cut them off above the cuff myself. It really made all the difference! The frumpy, Bermuda length ones can be very flattering when given the chop as they you can control the length and they already aren’t too fitted.

  42. Samantha says 5.19.17

    I have to DIY all my denim shorts to get around the same problem! I’ll buy a handful of jeans from a resale shop at the start of summer that fit in the waist and rear and then cut them to size myself. I cut them two inches longer than I want and fold up twice with an iron-in fabric hem tape inside to keep them done without a sewing machine. I do the same thing with the overly long ‘modest’ shorts since I’m 4’11” and they come to my knees!

  43. Bry Jaimea says 5.20.17

    I hear you loud and clear! I grew up in Australia and every summer was the tired old attempt to find the perfect denim short and finding them either too frumpy or too tiny. Thankfully now I’m in Scotland there’s no such need for them!

  44. Sara says 5.20.17

    I’m a 30-year-old Mom of 2 so I know exactly what you mean…I don’t want to wear anything too “junior” or too “old lady”. I just got the TopShop Ashley Ripped Boyfriend Shorts from Nordstrom and LOVE them! Plus, I like that they aren’t cuffed…sometimes a cuffed short feels like a lot of fabric around my legs. They do run a bit big, I ended up going down a size.

    • grace at the stripe says 5.22.17

      Haha exactly… I want to look cute and cool but also not like a child. Thanks for the suggestion. 😉

  45. Kathleen says 5.21.17

    The only pair I’ve found that I love is 7 for all Mankind cuffed ones. They are super stretchy (I had to size down and they’re still too big) and not too short even when cuffed. I have thicker thighs and they’re flattering!

    • grace at the stripe says 5.22.17

      Thanks Kathleen – I LOVE 7 so will have to check ’em out… maybe in store.

  46. Margie says 5.21.17

    I hear you! Also I refuse to pay the same amount as a pair of jeans. American eagle is my solution.

  47. Nicole says 5.21.17

    Could not agree more with this post, Grace! As a 19 y/o, I struggle to find shorts, especially denim, that are long enough to be appropriate but short enough to be trendy. I’m also 5’9, which makes it even harder. Usually I need at least a 3 inch inseam, and have yet to find a pair I like. I 100% support your idea to design your own… a business plan I’m sure would be successful!

    • grace at the stripe says 5.22.17

      It’s so hard! Definitely read through some of these comments – soooo many good suggestions.

  48. Susan says 5.21.17

    Yes. Yes. Yes. Anthropologie has the best selection! Not too short, not too tight, not frumpy, not torn to pieces… These:

    And not denim but these:

    And these (a million times cuter in person):

    I sized down one size in all three. The white denim (same style as above) was great in length but tighter fitting… on the plus side they were wonderfully NOT see through, but still too tight in my opinion.

  49. Anne says 5.21.17

    Parker Smith has cut offs with fringe, not destroyed, long enough to cuff or not. They are higher waisted so bending over is possible. A little bit of stretch and good quality denim. Not cheap but manageable in a world of wrecked shorts that are way too expensive and too short to wear.

  50. Melissa says 5.22.17

    Banana Republic Factory store has a pair that look similar to the ones you’re wearing but without the rips. They also stretch out so I have to wash them more often. The style this year is the same as last year so hopefully they make that style a staple.

    • grace at the stripe says 5.22.17

      Thank you so so much for the suggestion!!! I might have to scoop these up, ASAP! Love Banana. 🙂 x

  51. Ugh, I have this problem too! I’ve even tried sizing up and that just makes it too loose in the waist so that is a whole other problem. I think I’ve decided they just aren’t for me, but you make them look so cute in this outfit! Hopefully the denim shorts gods will read your post and help us 30 year old ladies out 😉
    xoxo, Jenna
    Boston Chic Party

  52. Heather says 5.23.17

    I agree!! I’m 36, in good shape, and have 3 young kids. I’m not about to run around town and go out and about in scandalous shorts! Now in the summer, I mostly wear dresses. It’s one thing, easy, and I don’t mind looking a little over dressed. You can never be too well dressed right? My 3 yo daughter has picked up in this and now only wants to wear dresses.
    I did just pick up a pair of white shorts from old navy that fit surprisingly well and were a good length. Of course the price was fantastic.

    • grace at the stripe says 5.24.17

      It really should not be too hard! Will have to check out the Old Navy ones, I need a new white pair!

  53. Cindy says 5.23.17

    Love your espadrilles. No more of that color at JCrew?

  54. Cindy Beck says 5.23.17

    You look adorable and age appropriate. I’ve about given up on the shorts search. I do love your espadrilles, but couldn’t find them in the light color you have. Have you had them for a while and now J Crew doesn’t carry them??

    • grace at the stripe says 5.24.17

      Thank you! So yes, J.Crew no longer carries this color – mine are 3 years old. They bring them back every year and I love the new colors but definitely prefer my lighter color!

  55. Kelsey says 5.24.17

    I swear by my pair of AG “Hailey” shorts. They come in a few varieties and each wash can fit slightly differently so don’t write them off until you try the “ex boyfriend” fit with the rolled cuff in a distressed wash.

  56. Ellie says 5.25.17

    I have an old pair from LOFT that I really love and they’re a nice length (I’m most comfortable in JCrew chino shorts with the 4″ inseam for reference). I also have had my eye on the white ones at JCrew. I also think Uniqlo might be worth a look.

  57. Anna Wagner Schliep says 5.25.17

    Seriously! I’ve given up on denim shorts and stick to linen or plain ol cotton. So far I’ve found decent (non-denim) shorts at Old Navy and J Crew, and that’s it so I have all of 2 pairs to wear. Before finding those, I almost never wore shorts and either suffered it out in jeans or wore dresses. After spending years thinking I couldn’t wear shorts because of my legs I’ve now gotten over that and would like to wear denim shorts if only they didn’t all suck.

    • grace at the stripe says 5.26.17

      I think you probably just have to find the right pair. I think boyfriend shorts are the way to go 🙂

  58. Chelsea says 5.25.17

    I could not agree more! When you’re not comfortable letting it all hang out anymore and don’t want to be totally covered in long bermudas there aren’t many options! Seems like some other people have suggested this but I’ve started sizing up in pretty much all shorts. Gives a more relaxed fit and a little more coverage but not tom frumpy.

  59. cynthia triplett says 5.3.18

    Oh wow I ran accross your site today in my quest to find distressed denim shorts that are darker wash, not to short and not to distressed and it is impossible!!!! I can’t tell you how many pair I have ordered and returned or tried on in stores over the years and NONE have worked. I did however order a pair from Express this year and I received them yesterday and I think I’m going to keep them. Check them out they are “midi” length. They are darker wash, high rise (which I love) they are frayed but only little distressing other then the frayed bottoms. And no cuffs. I hate cuffs on shorts!!! Anyway I am gonna check out some of the other suggestions in this thread also!!!!!

  60. Tricia says 8.1.18

    Hi! How do the rag and bone boyfriend shorts fit? I’ve heard everything from 2 sizes too big to TTS! Thank you!

    • Haha the reason you’ve heard so many things is they change the sizing every year. I have every size from 27-30 (I’m usually a 28/29) This year, take your usual size or a size smaller.