The Surprising Menswear Trend Taking Over Women’s Closets This Summer

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When it comes to fashion trends, there are generally two types—those that are obnoxiously omnipresent and those that fly under the radar. The first camp announces itself loudly and is everywhere you turn. (Looking at you, Barbiecore.) You can’t decide if you love it, hate it or if you’re stuck in limbo because you just don’t want to wear the exact same thing as everyone else.

As for the more subdued trends? They pop up in your feed, or you catch a glimpse of that cool girl at the train station. There’s a mystery there, and that’s enticing.

One I’ve noticed gaining traction: the button-down shirt and boxer short set. And to be honest, I’m obsessed. Think: Tom Cruise in Risky Business, but with a bit more, uh, coverage.

We’ve seen everyone from style influencers (like Pernille Teisbaek) to chic celebs (like Gabrielle Union) take on the look, and here are nine iterations that deserve a spot in your wardrobe.

ayr boxer shorts sets

1. Ayr The Deep End Shirt And Staycation Shorts

This crisp cotton shirt is going to become your new favorite button-up, with or without the shorts. But when do you sport this duo as a set we suggest pairing it with gold jewelry, a simple crossbody and flat sandals or sneakers to help differentiate from your PJs.

eileen fisher boxer shorts sets
Eileen Fisher

2. Eileen Fisher Puckered Organic Linen Shirt And Shorts

We adore linen for its breathability and cooling feel but could do without the need to iron or steam it every time we wear it. This lightweight shirt-and-shorts combo has a woven texture that won’t wrinkle nearly as much, so you can feel confident you look as good as you feel, no matter what’s on the agenda.

everlane boxer shorts sets

3. Everlane Linen Billow Blouse And Boxer Shorts

This collarless button-up with ¾-length sleeves is a more feminine twist on the typical masculine button-down. P.S. There is also a matching button-up short sleeve if that’s more your style.

lake boxer shorts sets

4. Lake Pocket Shorts Set

Those contrasting pockets on the top are a fun, unexpected detail that will make this set (and you) stand out from the crowd at your next park picnic or brunch date.

Size range: XXS to XXL

aritzia boxer shorts sets

5. Wilfred Free New Sail Shirt And Shorts

Both the shirt and the shorts come in a wide variety of colors, including Barbie pink, classic white and the cooling blue above. But don’t fret if your favorite is currently sold out, Aritzia restocks fairly often, so it’s sure to be back in soon.

recreational habits boxer shorts sets
Recreational Habits

6. Recreational Habits Martha Shirt And Ferry Shorts

Did we mention this trend also doubles as a super chic beach cover-up? Plus, it’ll save space in your suitcase since you can also wear both pieces out on the town before you hit the pool deck.

summersalt boxer shorts sets

7. Summersalt Going Places Gauze Top And Shorts

The 100-percent organic cotton material used to make this set is supremely comfy and beautifully lightweight to keep you looking and feeling cool all day long. The shorts also have pockets large enough to fit all the essentials, so you can run out to the store sans purse.

asos fashion union boxer shorts sets

8. Fashion Union Wallpaper Floral Shirt And Shorts

We love this twist on classic vertical stripes, and the fact that the top has ¾-length sleeves that flare a bit at the elbow for a gorgeous silhouette. You could even wear it to the office with a pair of dark-wash jeans and pointy-toe flats (although we’d save the shorts for weekends only).

abercrombie boxer shorts sets
Abercrombie & Fitch

9. Abercrombie & Fitch Oversize Poplin Button-up And Shorts

This oversize button-up is an Abercrombie best-seller that comes in so many different colors—including solids and a variety of stripes—you’ll have a hard time picking just one to add to cart.

zulu zephyr boxer shorts sets
Zulu & Zephyr

10. Zulu & Zephyr Signature Shirt And Shorts

Bold colors and stand-out stripes not your style? Opt for a classic white cotton duo. You can even lean further into the Risky Business vibes with some white ankle socks and wayfarer sunnies. Or go the opposite route and sport sexy lace-up sandals and shoulder-grazing statement earrings.

purewow author

Senior Editor

From 2021-2021 Dominique Hobdy held the role of Senior Editor covering all things fashion, trends, sales and more.



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...