Six Boxer Shorts Outfits That Prove They're Great for Summer Style

I’ve always found summer shorts difficult to find. I am extremely picky about their silhouette, comfort, weight, and rise. I know I’m not alone because I’ve heard people I style, friends and coworkers say that shorts are a summer pain point, and some even simply have decided to stop the quest for the perfect pair.

I dipped my toes into athletic shorts last year but their waistbands tend to hit too low for my liking, their material is too casual and sporty, and they tend to be short. My almost accidental introduction to cotton boxers as outfit-worthy (I wore a pair of my partner's last summer) has me convinced they are the perfect summer shorts. They have the perfection that a crisp button-down has, but for your bottom half. The right pair is 100% cotton, flares out a bit, and has a nice, high-rise comfy stretch band waistband. They’re breathable for the hottest of summer days and they pair well with absolutely everything; they’re especially fun to dress up. I’ve come here to prove my case, so keep reading for six boxer shorts outfits that just might finally pull together your summer style dilemmas.

The Favorite Classic White Poplin Shirt, Turned Boxers

You may have seen these on Instagram, as they’re so popular they’ve sold out several times. La Boxer Classica shorts by Comme Si (side note, a fantastic sock brand) are 100% Italian cotton poplin, just like your favorite crisp white shirt. They come in three colors, but my favorite is the white. They are shockingly not see-through, and are incredibly versatile, flaring out just a bit with a cool classic boxer double button and center band label. I like styling mine with a summer cardigan, pearls, and some casual sneakers.

The Summer Shirt in Shorts Form

These boxers are lightweight with a soft, barely-there cotton waistband, have a subtle print, and are under $10. 100% cotton, they’re breathable and airy. I like the idea of pairing such a classic boxer with loafers and a floral, scalloped top.

The Go-To Summer Set

I was immediately drawn to the shape of these 100% cotton boxer shorts by Recreational Habits. They’re a bit shorter than a classic boxer and flare out a bit extra, so I think of them sort of as a bloomers/boxers hybrid. The length is a bit short for a classic boxer, but paired with an oversized shirt (like the matching one available from the brand), the silhouette of your outfit remains flowy, loose, and cool—plus, they have pockets. They make half of the perfect summer set, and are even great over a bikini as a cover-up.

The Summer Set for Turning Heads

When on my quest to beef up my boxer wardrobe, I came across these by Andamane. I had been wearing my Uniqlo ones occasionally with strappy cropped tops, and when I saw that these boxers had a coordinating bra top, I was sold. The boxers themselves are the absolute ideal shape: high-rise, medium length, and I love the buttons and absence of branding or label. I personally own the black pair because I wanted a style I could really dress up. I like wearing the bra under my grandmother’s short sleeve blazer and some gold jewelry, but for more coverage, I would also wear it over a button-down shirt (like so). I feel really put together with a touch of sexy wearing this set.

The Statement Pair

Similar to the shape of the Recreational Habits boxers, these from Entireworld are a bit shorter and bubble a bit like a bloomer (which I am one to wear). I love how the khaki color looks paired with a crisp black tee, fun loafers or classic sneakers, and maybe hoops or a classic gold chain necklace. It’s an easy summer boxer shorts outfit that’s really just swapping denim shorts for something more fun and a whole lot more comfortable.

The Repurposed Classic Boxer Shorts Outfit

These classic chambray boxers from COS are just… boxers. If you’re looking for a staple that’s incredibly versatile, or want to just dip your toes into the boxer shorts outfit universe but not be so outright with the fact you're wearing boxers (these have no label or buttons), these are a great option. Lightweight and 100% cotton, they’re great worn with a tank, blouse, or tee. I personally envision these with a crochet top (go for either of the styles below, or find one that speaks to you) and strappy sandals or heeled dainty mules.