5 Ways To Wear The Boxer Shorts Trend This Summer

From Emma Corrin wearing Miu Miu pants at last year’s Venice Film Festival to Bella Hadid’s tighty-whities and UGG boots, the underwear as outerwear trend has seen multiple iterations over the last few years. But if you’re less inclined to wear lingerie outside (I don’t blame you!), you might be pleased to know that a comfier, less exposing alternative to the celebrity no-pants look has taken off this summer: boxer shorts. The perfect mix between shorts and pyjamas, the menswear-inspired undergarment is a trendy summer staple that comes in a wide range of styles including classic boxer briefs, oversized fits, and linen, cotton or silky fabrics. And: They’ll have you looking cool and feeling cool — because dressing for hot weather is no joke. 

Like similarly inspired menswear silhouettes that are in style right now (see: long denim shorts and tailored waistcoats), boxer shorts can be tricky to wear and style. They can ride up when you sit down, may not accommodate all body types, and can feel too casual for certain settings. That’s why I took matters (and a few pairs of boxer shorts) into my own hands by styling three pairs for five different occasions. Scroll on to discover how to wear the trend without looking like you’re ready for bed, and where to buy your own.

Boxer shorts and a baby tee go together like ice cream and a cone on a hot summer day. It just makes sense. Here, I went for a trendy graphic tee and paired the fit with tall boots and a metallic handbag. This is a perfect fit for something casual like a music festival (although I might reconsider boots depending on the terrain).

While I had my doubts, I actually managed to style boxer shorts for work. While this heavily depends on your office dress code, these Free People shorts are great for work because they’re oversized and the dark colorway generally looks more professional than the standard colored boxers. To dress them up, I paired them with a cotton shirt and leopard print ballet flats. For cooler days I’d add a blazer or leather jacket.

What I enjoyed about this pair from Pleasing is that it comes with a matching vest, with both made from a thick, opaque cotton — so I didn’t feel like it was too thin or inappropriate for outside. Plus, pairing the matching set with a blazer and bright-colored accessories helped to elevate the whole look. I’d gladly wear this to a shopping date or casual drinks with friends.

After styling the trend for a few days, I’ve come to realize that I will get the most use out of my boxer shorts while running errands, i.e., carrying loads of bags and stopping for a coffee as a treat. For a more casual outing, you can mix and match boxer shorts with practically any basic T-shirt or tank top and a light button-down for extra coverage, and complete the look with a pair of sneakers.

Admittedly, I stole this waistcoat-and-boxers look from Pinterest — and I’m happy I did. This outfit will be on repeat for the rest of summer and early fall because it’s versatile and pairs well with several types of shoes including trainers, heeled sandals, and knee-high boots. I’d wear this look for an al-fresco dinner or any kind of social plans.