In the name of comfort and ease, we have collectively graduated to the *actually* good pull-on short era, without any shame (even my younger team agrees, this isn’t a middle-aged thing anymore). Now, admittedly, I think that a lot of these can look like boxers or pajama bottoms if not styled, but once I took the time to add a few simple things, I’m convinced there is no need for stomach-constricting buttons or zippers this summer (besides my favorite two pairs of jeans shorts – these and these). From casual to even fancy, here are the pull-on shorts I thought were absolutely 10/10s (and I tried on A TON). BTW, if you haven’t checked out the shop page recently, head over there to find even more of my best fashion recs.

Linen Shorts | Linen Shirt | Straw Hat | Huaraches | Sunglasses

Linen? Check. Classic pattern? Check. Comfort, high quality, and affordable? Check. These pull-on shorts from Quince have a nice trouser vibe despite being elastic waist (and it’s a soft elastic, and it doesn’t cut in). These look good soft and wrinkled, so also great to travel with (and I will). I’m embarrassed to say that the shoes and shirt are also Quince (only because I think I’m more creative than just buying from one brand – but they are all so good). I’m wearing a small in the shorts and the shirt. The hat is a weekend staple.

Camo Shorts | Linen Shirt | Scarf (similar) | Boat Shoes

I’ve had these for a while (along with the pull-on pants version), and they are FANTASTIC in style, comfort, and shape. Please size down (these are an XS). They have a slight flair, which I think is crucial to making the leg look nice. I wouldn’t say they are polished (they are camo after all), but I do think you could throw a linen blazer on and it could count for casual Friday wear. I wear them all the time.

Eyelet Shorts | Puff Sleeve Shirt | Mary Jane Flats | Woven Bag | Woven Hat

How cute are these eyelet pull-on shorts? Think brunch or poolside, but could be dressed up with a white linen top and a cute bag (which I kinda did here). They have a thicker waistband that sits a bit higher – it’s not super tight or anything, but if you like a casual low-waisted fit (like the first two), know that these have more structure (great for long-torso’d folk who love high-waisted shorts and pants). The blouse is the raspberry version of the white one that I wear so often. I’m also so excited about that red purse.

Cotton Gauze Shorts (S) | Cotton Gauze Top (XS) | Belt Bag | Leopard Sandals | Sunglasses

I was seriously worried that this Gap set would look like pajamas (or like I was in a cult). But once I styled it out, I was VERY into it. It’s soft, gauzy, breathable, and the elastic waist is gentle and can sit high or low-waisted. It came in navy, white, and black too (some sizes were sold out). I’m wearing an XS top and S shorts. I LOVE the leopard pattern (on the sandals) with this set.

Pattern Shorts | Crop Button Down Shirt | Belt Bag | Platform Sandals | Straw Hat

I was so annoyed that, of course, the cutest and fanciest pull-on shorts are also a bit splurgier, but these guys are SO CUTE. I’m wearing a medium, and the fit is fantastic and yet doesn’t wrinkle (I haven’t washed them yet). They aren’t silk, but they feel like it, with more structure (the leg flare is fun and flirty). I feel like these could be great city shorts and vacation shorts because they look really polished and high-end.

Cotton Shorts | Tank Top | Cotton Cardigan | Sneakers | Woven Hat | Crochet Bag

I thought these pull-on shorts would fall in the “boxer” category, but look what styling can do!! They are higher-waisted, and the elastic is tighter (I’m wearing a small, and it’s a bit tight for my tummy, so size up or skip if you carry weight there). But if you can generally wear a higher-waisted short like these, they are super cute. (And my Gen Z team wants you to know that the boxer look is the actual look :))

Linen Shorts | Linen Shirt | Target Bag (In-Store Only) | Scarf | Huaraches | Raffia Cowboy Hat

Cheers to Target for designing a fluttery, flirty, drapey, soft, and oddly high-end looking linen pull-on shorts (the strings give The Great). Paired with the linen shirt and yes, the beach bag (which I could only find in-store at Target right now, sorry!) I’m absolutely going to be wearing this so much this summer. I was so comfortable, it was so breathable, so cute, and nothing cut in. I felt like I was absolutely wearing pajamas.

Chambray Shorts | Linen Shirt | Checkered Vans | Trucker Hat

Another pair of drawstring, easy-to-wear shorts that would be great with a little tank top, or if you are like me, a drapey linen shirt. These needed dressing up IMHO because they did really look like boxer shorts before I paired them with the blouse and Vans. They are great with a suit, too – just so thin, with cute stitching and a nice drawstring (a tiny bit of elastic, but it’s super soft). These come in a lot of colors, btw.

Linen Shorts | Linen Shirt | Woven Hat | Belt Bag | Platform Sandals

For those of you who don’t want a teeny tiny short, I was sooooo impressed with this pair from The Gap. They are more mid-length, but had a really nice 6″ hem that made the look more high-end and were still so relaxed, breathable, and comfortable. BTW, I go back and forth between the J. Crew linen shirt (with the pocket) and the Quince linen shirt (no pocket). Both are pretty perfect. The J. Crew is 10% better in drape and pocket, but it’s twice as expensive (but on sale right now).

Denim Pull-On Shorts | Linen Shirt | Huaraches | Hat (no longer available)

Denim Pull-On Shorts | Linen Shirt | Huaraches | Hat (no longer available)

No pull-on shorts post would be complete without an elastic-waisted denim short. The Gap delivered here. These are so comfy you could ride a bike in them (they have a lot of stretch). I’m wearing a small, which fits, so it’s pretty true to size, but if you are in between, maybe size up, not down. The elastic waist is soft and gentle, but it does look like elastic, so it’s better for no-tucking. These are extremely comfortable (and come in a few different washes).

If you are looking for great sandals to pair with your cute and easy pull-on shorts, I did a big review post here, or you can see those and all our other great shoe picks here.

*Photos by Kaitlin Green