How To Wear Boxer Shorts: Cute Outfits, Inside


Boxer shorts are the best alternative to denim cut offs that I’ve seen in a long time. If you have any reservations about wearing a pair this summer, let’s just think about it for a moment…

…a lightweight, soft material

…an elastic waistband that moves with you

…a length that isn’t going to show your cheeks when you bend over, but isn’t so long they’re impossible to style (aka a happy medium)

Not to mention, skipping this oh-so-easy trend would mean missing out on the comfiest outfit of the summer. TRUST ME on this one (but, uh, if you don’t – I have outfit ideas to further convince you, keep scrolling)

shorts (M) | top (L) | sandals

Everyone Needs Boxer Shorts For Summer (And Here’s How To Style Them)

Boxer shorts are trending, but this doesn’t mean you have to wear an actual pair of mens boxers (although I can personally attest, mens boxers are just as fun and almost always the cheapest option). Any soft, cotton-adjacent, elastic waistband short works really well for trying out this popular summer look. 

shorts (M) | top (L)

J.Crew made the pair I first scooped up last summer to give this trend a go, and thankfully they’re in stock again this year. These shorts have that classic boxer style look, complete with the pretty little J.Crew logo on the waistband, but the open fly is just for looks (aka, it’s sewn shut). 

I have since collected quite a few pairs of boxer shorts from various brands, but almost none are as good of quality as this pair. PLUS, they don’t wrinkle as easily as all the other boxer shorts I own – and when they do collect wrinkles, they can be spritzed with water and thrown in the dryer with no worry of shrinking.

shorts (M) | top (L) | sandals

While the current fashion landscape is giving us a real deal excuse to essentially wear pajamas as a certified stylish outfit, actually styling them in a daily outfit is not nearly as hard as you might think.

Throwing an oversized button-down on with your shorts is hands down one of the most simple ways to wear them (which works for both everyday looks or even as a swim coverup), but boxer shorts are arguably just as versatile as a denim short. 

shorts (M) | top (L) | sandals | bag

3 More Spring & Summer Outfit Ideas With Boxer Shorts

The key wearing boxer shorts is to lean into the soft + comfy…but offset with an elevated piece (or two) to make the look intentional – not unlike denim short styling! Here’s a few other ways I’ve been wearing my boxer shorts:

Outfit Idea 1: Boxer Shorts + Cotton Sweater + Leather Slides

shorts (M) | sweater (L) | tee (S) | sandals

The first way I styled boxer shorts last spring is still one of my favorite, go-to outfits: shorts, a structured white tee, and an oversized sweater layered on top. This look leans soft and comfy just as the boxer shorts do, but doesn’t actually look like you’re rocking your pajamas out and about.

PS – my mom has this dupe of the sweater I’m wearing and it’s truly just as good for a much better price point…plus, actually in stock.

Outfit Idea 2: Boxer Shorts + Hoodie + Sambas

shorts (M) | hoodie (L) | hat | sneakers

Although, let’s not kid ourselves, sometimes that pajama-adjacent loungewear feel IS what I want to wear all day. In that case, a hoodie (this is the worlds best hoodie, IMO) and well-worn sneakers is my favorite combination. 

Outfit Idea 3: Boxers + Flowy Cotton Blouse + Ballet Flats

shorts (M) | top (M) | flats | bag

For something a bit more chic, I love pairing a flowy cotton blouse with boxer shorts. The look feels equal parts feminine and masculine, which gives you almost an endless option of shoe pairings, depending on how you want your overall look to flow (a simple ballet flat is my personal fave). 

These flats were among the most comfortable mesh flats that I tried earlier this year, and now Target just came out with an extremely similar version of their own. I can’t say I’ve tested the Target pair myself, BUT – memory foam.


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