30 CUTE Pull-On Shorts For Our Most Comfortable Spring/Summer Yet

The time of year is upon us when we tend to start thinking about shorts. We get to free our bottom limbs and run free! But we must not forget that traditional jean shorts are not the only option. Actually, let’s just get rid of zippers and buttons entirely! That’s right folks, I’m talking about cute, fashionable, comfortable pull-on shorts. In the words of Kim Cattrall, “I don’t want to be in a situation for even an hour where I’m not enjoying myself”. While she wasn’t necessarily talking about zippered/buttoned shorts, it could easily be included in the meaning. Pull-on shorts are inherently the most comfortable and least restricting type of shorts. The team has been singing their praises for years. But for some reason, we’ve only ever done posts dedicated to the more athletic versions. Well, that stops today because we are on the hunt and thought you might be too. Let’s start.

Mila Linen Short – $98

These were the shorts that inspired this post. Marlee was the one to actually suggest this post idea because she had just started her pull-on short search. Naturally, we all agreed it was a great idea because we love a pull-on short and these ones were total winners. They are a little more expensive, but are sustainably made (from Reformation), and are so classic that they will never so out of style.

High-Waisted Paperbag Waist Striped Short – $42

For a similar stripe with a little more going on detail-wise, how fun are these?! I love the frayed hem, the paperbag waist, and how the stripes also have a little design within them. These would be great to throw on around town or perfect next to a body of water. Perfect for at home or on vacation. They also come in a solid patterned cream version (you’ll get what I mean when you look at them).

Damson Madder Krissy Linen Blend Boxer Shorts – $85 | New Mariner Jersey Short -$60

Damson Madder is a very cool London-based, sustainable brand that my cool friend told me about last year. Needless to say, I was happy to see that Anthro did a collab with them! They are known for their fits and these shorts are so freaking cute. Definitely in the world of the boxer shorts trend but a little more refined. But if you love the red stripe look but want more of a nautical feel, these J. Crew ones are awesome. Vibrant but classic.

Farm Rio Palm Tree Shorts – $198

FYI, these shorts are the most expensive on the list but also…look at them. These heavenly beauts are SO fun and since they’re from Farm Rio, I know without a doubt super high quality. The details are so special! It is a part of a set (here’s the top) but these could easily be worn with so many other tops. A loose white button-up would be effortless. These definitely give “vacation” but I say let home feel like a vacation too when you pop these cuties on.

La Ponche Linen Pull-On Shorts – $98

Another fun option! I love the color (but they also come in sand with a plus size option), that statement tie at the top, and the stitching. Plus, the length is so nice. No chance of those cheeks saying hello:) They are just a little more tailored and special than your average pull-on short.

Organic Cotton Poplin Boxer Shorts – $39

Sorry for the blurry photo but it was the best I could do. Anyway, how great is that green! These are also in that boxer short trend category which I am very tempted to try. They just look so damn comfy but also cute. I know it’s not for everyone but at the price I might give it a whirl. Plus, so great for poolside, right? (But can we also talk about the cuffs of the top??)

Miramar Cotton Terry Walking Shorts – $98 |  “Denim” Sweatpants

I’m going to be honest, I didn’t know about the viral “denim” sweatpants Em was wearing in this post until I looked it up after she talked about them. They sound INCREDIBLE. So when I saw they had a shorts version, I HAD to include them. Duh. They come in three different washes (one lighter and one darker than the one pictured above), and if they are nearly as comfortable as everyone says the pants are, these are a homerun.

Easy Denim Shorts – $47 | Stretch Ruffle Short – $37

But if you want a pull-on short that isn’t printed to look like a jean but is still comfy here are two great options under $50. The ones on the left do not have any stretch (aside from the elastic band) but will give you a cool relaxed look. Love that wash color. Then those cuties on the right have that sweet ruffled hem. They are also lower rise so keep that in mind whether that’s your preference or not.

Denim Pull-On Shorts – $72

A Madewell soft, denim boxer short? Sign me up! Easy, soft to the touch, cute, and made with their “summer-friendly cotton-blend Airy Denim”. That means they are perfect for the warmer weather. I also know Caitlin and Arlyn have been big fans of Madewell’s pull-on shorts in the past.

Linen-Blend Pull-On Short – $25

Why yes, you can be this chic for $25;) I mean get outta here, right? These tonal stripes and that sleek waistband are so good. Just enough color without it looking too bold. You could wear these to the office or on vacation, easily. They also have a bunch of other colors and pattern options if you are interested:)

Pull-On Shorts – $54

More “boxers” but that pocket is so cute! I just couldn’t resist. Also from Madewell, also super light and also extremely comfortable.

Alexis Stripe Cotton Drawstring Shorts – $78 | Beach Short – $64

These two feel less boxer-like to me because of the cuts (absolutely love how the sides are shorter) and the drawstring detail. The dark navy ones also come in a bright green and the light blue ones have a matching button-up top. These are great swim coverups too!

Zoey Linen Short – $98

And if you love a drawstring but not a print, these Reformation shorts are beautiful. So simple but so versatile. They come in three other neutral colors and these would be a breeze to dress up or down.

Pull-On Drawstring Shorts – $78 | High-Waisted Linen-Blend Shorts – $22

For some additional solids, I adore the pockets on the Madewell cuties on the left. They come in 5 other color and pattern options but the style is what really makes them look less like a pull-on and more like a “normal short”. They’ll never know how comfortable you are! Then for a steal at $22, these Old Navy ones are the perfect throw-on-and-go pair that also come in seven other colors:)

Seersucker Pull-On Shorts – $15

Aside from the sweet gingham print (it also comes in a butter yellow) I really love the texture of these shorts. They are made to look super relaxed and boy do they. Also, that price? SO GOOD.

Pull-On Poplin Shorts – $68 | High Waist Stripe Cotton Blend Drawstring Shorts – $88

More Stripes but with really fun details! The contrast pattern trim on the pockets and the cuffed bottoms on the left shorts make me want to add to cart immediately. Then if you like a little metallic moment in your pull-on shorts there is a silver thread in the shorts on the right you’ll love. Fun but neutral:)

The Somerset Shorts: Linen Edition – $98

Stripes aren’t the only pattern we love. These floral cuties are so fun! They come in seven other colors in petite, standard and plus sizes. The options are endless and CUTE.

Mid Rise Linen-Blend Pull-On Short – $50

Would you believe these are Abercrombie? I know we’ve been raving about their evolution for a minute but it’s still so exciting! These mid-rise (yes!)summertime linen shorts are playful, chic, and highly rated. If shells aren’t your style they have seven other options to choose from.

High-Rise Paperbag Skort – $75 | Offbeat Printed Pull On Short – $78

The florals continue on:) Not really sure why the shorts on the left are being called a skort because in every photo they really look like shorts but I wouldn’t be mad about either way. Love the high waist, the flowy bottom, and that subtle but playful print. I think if I had to choose a floral short it would be these ones on the right Read More