In the name of comfort and spontaneity, we’ve collectively reached a younger era of *really* good pull-ons, without shame (even my youth team agrees, this isn’t a middle-aged thing anymore). Now, admittedly, I think 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 was convinced that there is no need for belly-buttons or zippers this summer (besides my favorite two pairs of jean shorts – in And in). From casual to fancy, here are the pull-on shorts that I thought were an absolute 10/10 (and I tried on a ton). By the way, if you haven’t checked out the shop page recently, head over there for more of my best fashion intel.
linen shorts | linen shirt | straw hat | Huaraches | sunglasses
Linen? check. Classic pattern? check. Comfort, high quality and affordable? check. in Pull-On Shorts from Quince There’s a nice trouser stretch despite having an elastic waist (and it’s a soft elastic, and it doesn’t cut). These look soft and wrinkled, so they’re great for traveling with (and I will). I am ashamed to say that Shoes And shirt There’s also Quince (only because I feel like I’m more creative than just buying from one brand – but they’re all very good). I’m wearing a short one in shorts and a shirt. Cap A weekend staple.
camo shorts | linen shirt | scarf (similar) | boat shoes
I’ve had in for a while (together) Pull-on pant version), and they are fantastic in style, comfort and size. Please size down (these are an XS). They have a little bit of ease to them, which I think is important for making the foot look good. I wouldn’t say they’re polished (they are camo, after all), but I think you can wear a linen blazer and it can count as casual Friday wear. I wear them all the time.
eyelet shorts | puff sleeve shirt | Mary Jane Flats | woven bag | knit cap
they are so cute Eyelet Pull-On Shorts? Think brunch or poolside, but dressed up with a white linen top and a cute bag (which I did here). They have a thick waistband that sits a little high—it’s not too tight or anything, but if you prefer a relaxed low-waist fit (like the first two), know that these have more structure (great for guys with a longer torso who prefer high-waisted shorts and pants). the blouse is raspberry version The white one I usually wear. I’m very excited about it too red purse.
Cotton Gauze Shorts(S) | Cotton Gauze Top (XS) | belt bag | leopard sandals | sunglasses
I was seriously concerned about this gap set Pajamas would look like (or like I was in a cult). But once I styled it, I became very interested in it. It’s soft, shiny, breathable, and the elastic waist is supple and can sit high or low waist. It also came in navy, white and black (some sizes sold out). i’m wearing one xs top And s shorts. I love leopard pattern (on) slippers) with this set.
pattern shorts | cropped button down shirt | belt bag | platform sandals | straw hat
Of course, I was very angry with this The cutest and coolest pull-on shorts They are a bit expensive, but these people are very sweet. I’m wearing a medium, and the fit is great and still doesn’t wrinkle (I haven’t washed them yet). They’re not silk, but they feel like it, with more structure (the leg flare is fun and flirty). I think these could be great city shorts and vacation shorts because they look really polished and high-end.
cotton shorts | short top | cotton cardigan | sneakers | knit cap | crochet bag
I thought These pull-on shorts Would fall into the “boxer” category, but look what the style can do!! They have a higher waist, and the elastic is tighter (I’m wearing a small, and it’s a little tight for my stomach, so go up or down a size if you carry weight there). But if you can normally wear high-waisted shorts like this, they look super cute. (And my Gen Z team would like to tell you that the boxer look is the real look :))
linen shorts | linen shirt | Target Bag (in-store only) | scarf | Huaraches | raffia cowboy hat
Kudos to Target for designing something flirty, flirty, drapey, soft, and weirdly high-end. Linen Pull-On Shorts (gives the telegram Great). paired with linen shirt And yes, the beach bag (which I could only get in stores Target Now, sorry!) I’ll definitely be wearing this a lot this summer. I was so comfortable, it was so breathable, so cute, and there was nothing cut in it. I felt as if I was wearing pajamas.
chambray shorts | linen shirt | checkered van | trucker hat
Another pair of drawstrings, easy-to-wear shorts It would be great with a little short topOr if you’re like me, a drapey linen shirt. IMHO these needed to be spruced up as they really looked like boxer shorts before pairing them with the blouse van. They also look great with a suit – absolutely thin, with beautiful stitching and a nice waistband (a little bit of elastic, but it’s very soft). Well, they come in lots of colors.
linen shorts | linen shirt | knit cap | belt bag | platform sandals
For those of you who don’t want a tiny short, I was very 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 still were very comfortable, breathable, and cozy. Well, I go back and forth between J Crew Linen Shirt (with pockets) and Quince Linen Shirt (No pockets). Both are quite perfect. J. Crew is 10% better in drape and pockets, 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 this elastic-waist denim short. Gap delivers here. These are so comfortable you can ride a bike in them (they have a lot of stretch). I’m wearing a small, which fits, so it’s true to size, but if you’re in between, maybe size up, not down. The elastic waist is soft and supple, but it looks like elastic, so it is better for no-tucking. These are super comfortable (and come in a few different washes).
If you’re looking for great sandals to wear with your cute and easy pull-on shorts, I’ve posted a huge review here, or you can check them out and all of our other great shoes here.
*by photos Caitlin Green
