Finding the right pair of denim shorts has been a struggle for me summer after summer. Instead, I tend to stick to skirts, dresses, and jeans because I’m rarely able to find a pair of denim shorts that make me feel totally comfortable and confident.
Gap Denim Shorts Are My Latest Obsession
I feel like I’ve tried them ALL and no other brand has come close to hitting all the marks for me like Gap’s denim shorts. Not only are they super-affordable and often on sale, but Gap also carries a bunch of styles and sizing options including petite, regular and tall with sizing up to 35. They also offer a variety of inseam lengths as well as high-rise, mid-rise and low-rise styles. Honestly, what more could I ask for?? Let’s check out the five pairs I tried…
Yay! Gap is offering 40% off this Memorial Day Weekend. Use code SUNSHINE at checkout.
1. Gap 3″ Sky-High Cheeky Denim Shorts

Shorts (28) | Top (M) | Sandals (TTS)
These Sky High Cheeky Denim Shorts are EXACTLY the style, fit and wash I was after. I love the vintage, distressed wash, and the ultra high-rise fit.
Fit notes: Most of Gap’s denim shorts I tried fit pretty true to size, but these were a little snug. I could have done with ordering one size up from my usual size 28. Otherwise, they are PERFECT.
2. Gap 4″ High Rise Denim Shorts in Dark Indigo
Shorts (28) | Similar Bodysuit | Sandals (TTS)
These were the biggest surprise favorite of the bunch. I had to force myself to order a dark wash pair because everything else I ordered was light or medium wash, and distressed. When I put these on, I honestly did a double-take in the mirror. I couldn’t believe how flattering and classically chic these looked. Out of all the shorts I tried from Gap, these were probably the ones that fit the best. The denim is soft and has the perfect little bit of stretch to them, so they are comfortable but don’t stretch out. Definitely. Get. These.
Fit notes: I found these to be true-to-size and I’m wearing my typical 28s.
3. Gap 4” High Rise Button-Fly Denim Shorts
Shorts (28) | Similar Tank Top
These were another pleasant surprise.
Fit notes: The 4″ high-rise denim shorts are pretty much the perfect length and fit for me. While I love how the 3″ cheeky high-rise shorts look, I found the extra inch in length really helps here.
4. Gap 5” Mid Rise Boyfriend Shorts
Shorts (28) | Tank Top | Sandals (TTS)
Even though I’m definitely a high-rise denim girl, I ordered two pairs of these 5″ inseam, mid-rise boyfriend shorts just so I could say I gave them a shot. I was REALLY surprised by how much I liked these. This light wash is probably my favorite of all the Gap shorts I tried — it’s the perfect color for summer. The mid-rise will take some getting used to for me since I’m so used to hitching all my denim far up on my waist.
Fit notes: Overall, I liked the fit, as well as the length, but I wish I would have ordered a size smaller in them because they were loose in the waist. I ordered my normal size 28, but could have gone with a 27.
5. Gap 5” Mid Rise Distressed Boyfriend Shorts
Shorts (28) | Similar Tank Top | Sandals (TTS)
Like above, these are another pair of 5″ mid-rise, boyfriend shorts…just in a different wash (which I love).
Fit notes: I wish I would have ordered one size smaller than my usual 28.
Shop More Gap Denim Shorts
Xo,
Jess
Gap hasn’t failed! Getting these chk out right away before they sell out, you’ve sorted these so well, thank you!!
I totally agree! “Gap is back” 😉 Glad the post helped!
P.S. Also, they are pretty good about re-stocking sizes, so keep checking back if sizes are sold out!
Gap doesn’t list the rise. How many inches is the front rise on the high rise?
Gap’s denim game has been ON POINT this year!! I now need to try their shorts! Love all your looks!