Shorts That Don’t Suck

This blog post was originally posted on May 8, 2018 and republished with some new additions on March 28, 2019. Since shorts season is just about here, I thought you guys would find this post helpful as you prepare!

This post was a lot of fun to put together. It was, for sure, a labor of love, and I can’t even tell you how many pairs of shorts I tried on for it… 40? 50 pairs? Maybe even more! But it was totally worth it because, as someone who has strong, muscular legs, I know how difficult it can be to find shorts that actually fit my thighs, don’t ride up, and drive me crazy. And, of course, I wanted to do my due diligence before making my recommendations to you all. 

In the past, I hardly ever wore shorts, and, if I did, they rarely went much above my knees. Over the years, I’ve gotten over my unhealthy obsession with hating my legs and have come to appreciate and maybe even enjoy wearing shorts. I’ve learned it’s all about finding shorts that move WITH you and make you FEEL great. Wearing an ill-fitting pair is one of the worst things ever. For real. I mean, how uncomfortable is wearing shorts that you’re constantly thinking about, pulling down and adjusting? Ugh, that’s the worst. Who has time for that nonsense? 

The shorts below are definitely more casual (lots of jean favorites), but all of them are wear-tested in real life and score high on style and, most importantly, comfort. I love all of the shorts recommended below, but I listed them in order of “obsession” with my top, top, top favorites first. I also included a bonus workout pair of shorts at the bottom, which are a tried-and-true favorite and might have even inspired another blog post: “Workout Shorts That Don’t Suck!” I hope you guys find these suggestions helpful and rock your shorts with confidence this summer! 🙂

Caslon Rolled Denim Boyfriend Shorts – Love, love, love! These rolled denim boyfriend shorts couldn’t be more comfortable! I love that they’re casual enough for everyday wear, but stylish enough for wearing out to dinner with friends. They come in both regular and petite sizes, and they’re priced right at $58. I see myself wearing them a TON this summer! I ordered them in a size 25, and they fit perfectly – a little roomy in the hips, but not droopy!

Very similar to the shorts above, but not pictured – only because I bought them last last summer – but worth a mention because they’re so darn comfortable and J.Crew still sells them. (I assume they were popular last year!) The High-Rise Denim Short in Brixton Wash (40% OFF FULL PRICE WITH CODE POPUP) is super flattering with the same rolled cuff style, but they have a slightly higher rise on the waist. I own them in size 25. Both pairs of jean shorts mentioned are great – it just depends what style you prefer.

Metro Downtown Shorts – I’ve mentioned these shorts a couple times on the blog already because they are so amazing! They’re insanely comfy, and I know I’ll wear these a ton – around the house, running errands, going on family hikes, and to the beach. They’re kind of a hybrid between a regular short and a board short, but the fabric is thick and stretchy, so they’re nice enough to wear everyday, but more casual and sporty. I originally ordered these in an XS, but ended up exchanging them for an XXS. If you’re in between sizes, I’d size down – they seem to run big.

Cabo Beachside Linen – I have my eye on these babies for summer. They’d be perfect for pre- or post-beach adventures, and they’re look great on tan legs! 🙂 The Trekkie Shorts from Athleta also grabbed my attention!

Every Day Shorts – How fun are these seersucker shorts? It was love at first sight with these babies, and they lived up to my expectations for sure. The fit, feel, and fashion came together perfectly with these shorts. They’re on the shorter side with a 3.5-inch inseam, but roomy enough that they don’t ride up. They also come in 5- and 9-inch options as well as a ton of colors and some prints. I own them in a size 4. I really like the Island Palms print! 🙂

Marla Ripped Cutoff Shorts – Another jean favorite! Hey, I can’t help myself! 🙂 These ones are a bit longer than the ones mentioned above, comfortably frayed, and a little stretchy. The cuff at the bottom can be rolled as high or as low as you’d like. I own these shorts in a size 2.

Caslon Cotton Twill Shorts – And here’s a non-jean pair of shorts! 🙂 These cotton twill shorts have a hint of stretch, so they’re fitted without being super duper tight. They come in regular and petite sizes as well as other colors. I ordered them in a size 2.

Brooks Chaser 3″ Shorts – An oldie, but goodie pair of shorts! I probably own 3 or 4 pairs of these shorts now, and they’re awesome for all kinds of workouts. They’re lightweight and semi-fitted, so they really move with you, especially over your thighs for movements like air squats, Cleans, Wallballs, etc. If you’re a fan of a longer short, Brooks makes a 5″ option. I own these in a size small.

Question of the Day

Love shorts? Hate shorts? What shorts do you especially love?

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22 Comments

  1. OMG! I LOVE this post! I agree, shorts for women with thighs are hard to find! Thanks for the suggestions!

  2. Thaaaaannnkk you! Ps: just ran for the first time in a brand new pair of those Brooks shorts. I got them for $32 on the REI website (somehow they’re back to full price right this second?) but the 7” are $28!

  3. Thank you for this post! I have “athletic” (on a good day!) thighs for being a size 6 and it’s so awful pulling on shorts that make my legs look like sausages.

  4. Thanks for putting together this post. I have thicker thighs and avoid wearing shorts because I have a hard time finding comfortable options. I am going to check a couple of these out.

  5. Great post, Tina!! As a Mom and a runner I have the same love/hate relationship with shorts! I’ll have to try some of these out. I’d definitely be interested in a “shorts that don’t suck-workout edition” too! I’ve been running for about 5 years now and I still haven’t found a pair of running shorts that I love!

  6. I love shorts, which is a good thing since I live in FL where they’re a necessity!
    I’m also apparently pretty lucky that Target shorts fit me pretty well since they’re cheap 😉

  7. Today I said I was putting myself on a shopping freeze. But I need some of these pairs!! Last summer I didn’t wear shorts at all (just dresses or my trusty Lulu gym shorts) I don’t think because I was so miserable in them. Blah!

  8. I was JUST talking to a friend at lunch about wanting shorts that didn’t feel like “mom” shorts but still fit well and were cute and comfy! This is perfect 🙂

  9. Thank you for this!!!! I have a big butt and smaller waist, so shorts are always riding up on me and it’s the most annoying/uncomfortable thing. I just bought two pairs of the Caslon shorts to see which size is best because they look legit.

  10. I have a pair from Gap I got years ago and I’ve been trying to find the same pair every sense! I love the look of those longer ones that are fitted.

  11. I’ve never worn shorts until I had my son and the park was TOO damn hot for workout leggings and I just wanted to be comfortable and proud of my body! So out came the shorts! I love this post so much because I always have an issue with the riding up and the length of shorts! Can’t wait to check these out!

  12. I hate shorts. I hate how they make my legs stick to the chair I’m sitting in. I hate how they ride up. I hate them forever. Thank you for sharing your favorites, though. I will stick to pants.

  13. I am not a shorts fan unless it is athletic shorts. Regular shorts always seems to cut into my legs weird when I sit down. Your post is making me think I should give more traditional shorts a try again though!

  14. I love these recommendations!! I need those Marla shorts planning on ordering ASAP.
    I did buy a pair of the 3” Brooks shorts and exchanged for the 5” length. I was fine with them until I started running, then realized they were too short for me once I started running. ☺️

  15. I’m not a fan of shorts because I’m super pale and feel self-conscious when wearing them. And when I walk into stores, I get super cold. I do like my legs and could do longer shorts.

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