Well. We made it to Friday, and I have almost no plans this weekend (besides 4 kids’ sports games). As I’m writing this, I’m in bed, sniffling, begging this cold not to latch, rewatching Ransom Canyon, season 1, in preparation for season 2. It’s SO GOOD. But denim shorts can’t wear themselves, and there are too many bad ones out there to avoid (Y’all, I tried on a lot and was surprised at the cuts). Turns out a few of my favorites from the last two years are still going strong, likely because they are solid in both quality, style, and flattery. You see, I think most of us don’t want to wear really tight denim shorts in the summer. Isn’t the whole point to throw them on and feel casual and cool? We don’t want them tight and constrictive. So here are my favorites right now – a few old and a few brand new.

Denim Shorts: Agolde Parker Long Shorts

Agolde Parker Long Shorts (size 27) | Shirt (size S) | Sandals

Agolde Parker Long Shorts (size 27) | Shirt (size S) | Sandals

While I wish my #1’s were as affordable as my #2’s (below), these Agolde Parker shorts will continue to go strong a third year, which I think says a lot. They have the perfect structure that sits softly on the hips and then flares out just a bit (I do not like a denim leg hug), which gives your legs some room and plays with your eye in a nice way. Man, they are good. They have a raw hem, but not much more distressing. They are a thicker denim that has almost no stretch and run a bit big (I’m wearing a 27 here and these still fit when I wore a 28 in most things).

Denim Shorts: Gap Mid Rise Loose Denim Bermuda Shorts

Gap 8″ Mid Rise Loose Denim Bermuda Shorts (size 27) | Shirt (size S) | Flats

Gap 8″ Mid Rise Loose Denim Bermuda Shorts (size 27) | Shirt (size S) | Flats

My second favorite denim shorts, for more of a longer profile, are these from the Gap. They are loose, not full “JORT” which I know a lot of us aren’t into (despite them being “in,” I’m like, are they really?). These are so easy to wear, and are extremely soft with some stretch (so they are very, very comfortable). These are their 8″ drop, which usually means pretty high waisted, but they don’t hug and pooch like a lot of high waisted do on me.

Denim Shorts: 90s Agolde Shorts

90s Agolde 7.5″ Shorts (size 27) | Blouse (size S) | Sandals

Now, these denim shorts are definitely JORTS, and listen, I feel cool wearing them because the color, fade, stitching, tailoring, and structure are really good (they are another pair of Agolde’s). These are best paired with flip flops or Sambas and an oversized anything on top or a tiny tank. I’m still really in love with these leopard sandals, BTW.

90’s Agolde 7.5″ Shorts (size 27) | Blouse (size S) | Sandals

Check out my comfortable sandal review here in case you missed it.

Denim Shorts: Free People Moxie Barrel Shorts

Free People Moxie Barrel Shorts (size 26) | Shirt (size XS) | Sandals

So good, y’all. SO GOOD. These denim shorts are more workwear, cargo denim shorts (so on the very, very casual side), and not to be dressed up. But so easy to throw on with sandals or sneakers and loose enough to walk around for hours or even bike. Definitely size down on these (I’m a 27 right now, and these 26’s are still pretty loose on me).

Free People Moxie Barrel Shorts (size 26) | Shirt (size XS) | Sandals

Denim Shorts: Pilcro Henri Denim Shorts

Pilcro Henri Denim Shorts (size 27) | Shirt (size S) | Flats

For all of you/us who might want to look a little more pulled together, these denim shorts are it. The two-toned denim looks polished, and they have a tailoring that feels like you care, with a cute brass button detail. Flattering, comfortable, and can absolutely be dressed up with some heels (kitten or platform).

Pilcro Henri Denim Shorts (size 27) | Shirt (size S) | Flats

Shout out to that Target blouse that I wore a ton during spring break (so lightweight it’s perfect for humidity). And new tortoise jelly flats that were sent to me by Steve Madden, and I now that I’m looking at them in the photos, I’m a bit on the fence!

Denim Shorts: Free People Now Or Never Denim Shorts

Free People Now Or Never Denim Shorts (size 27) | Blouse (size S) | Mules

For those who want to go “mini” but not “micro,” these denim shorts are GREAT. They are true to size (I ordered two sizes because I assumed they would be tight), but they are cut well and fit really nicely. They sit nicely on the hips, don’t cut in or hug too tightly, and flair out just a bit.

Free People Now Or Never Denim Shorts (size 27) | Blouse (size S) | Mules

They are distressed but not in a way that my father-in-law will make fun of me and ask me if I need to borrow money to buy real shorts 🙂 It’s a great light blue wash. And yes, those are the world’s most comfortable and still VERY cute mules.

Happy “jean short” season for all those who celebrate 🙂

*Photos by Kailtin Green