I Tried the Controversial Summer Shorts Trend Only Fashion People Truly Get

Nikki Chwatt wears four pajama shorts outfits. The first outfit is a pink top with pink striped shorts and white closed-toe mules. The second outfit is a beige vest with brown striped shorts, black flats, and a black Bottega Veneta bag. The third outfit is a striped polo shirt with blue striped shorts, socks, and black square-toe loafers. The fourth outfit is a distressed brown leather jacket, a beige vest, brown striped shorts, and beige loafers.

(Image credit: @nikki.chwatt)

Over the summer, my Instagram feed has been inundated with European and American fashion trendsetters taking part in the controversial pajama-shorts movement. While opinions on this trend vary widely, I prefer to judge fashion trends only after I've tried them. This is why I decided to experiment with the boxer-shorts trend and form my own opinion.

After trying out different outfit combinations, I began to understand why, according to Google Trends, there has been a surge in searches for terms like "poplin boxer shorts" and "women's boxer shorts" in the past month. A new wave of fashion-forward women seems to be embracing these bottoms because of how lightweight and comfortable they are for all-day wear, which are ideal traits for sweltering temperatures. Plus, they lend an abundance of styling possibilities. These versatile bottoms are perfect for any occasion, whether you're meeting friends for brunch or adventuring in a new city.

If you're curious about how to style boxer shorts in unique and chic ways, keep reading. Ahead, I've put together tasteful and thoughtful outfit ideas that go beyond pairing the shorts with the matching button-down shirt.

1

Nikki Chwatt wears red striped shorts, a white button-down shirt, a white t-shirt, burgundy loafers, and a beige trench coat.

(Image credit: @nikki.chwatt)

The best part about the boxer-shorts trend is how versatile it is. Creating a transitional outfit is a straightforward way to get more use out of the shorts. Grab a long trench coat and a button-down shirt. This combination effortlessly makes the bottoms fall appropriate.

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2

Nikki Chwatt wears brown striped shorts, a beige sweater vest, black caged sandals, and a black Bottega Veneta bag.

(Image credit: @nikki.chwatt)

Boxer-style shorts have become increasingly popular, and a unique and modern way to wear them is by pairing them with a knitted vest. This stylish combination creates a sophisticated silhouette that perfectly balances casual and chic. While many might opt for chunky sneakers, I enhanced the outfit by pairing it with fisherman-style sandals, adding a visually appealing and unconventional touch.

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3

Nikki Chwatt wears a denim shirt, navy striped shorts, and black ballet flats.

(Image credit: @nikki.chwatt)

I've been eyeing the British brand Aexae for a while now, so when I was researching pajama-inspired shorts and came across its striped iteration, I knew it was the perfect opportunity to test it out.

The bottoms have an oversize fit, so I paired them with a fitted denim shirt to create a well-balanced look that exudes an elevated yet minimalistic style. To maintain this aesthetic, I completed the outfit with classic ballet flats. This outfit formula is one I highly recommend re-creating because it's simple but fashion-forward.

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4

Nikki Chwatt wears blue striped shorts, a striped polo shirt, ivory ankle socks, and square-toe black loafers.

(Image credit: @nikki.chwatt)

I tend to opt for simple outfits, but whenever I come across a stylish, bold ensemble on my Instagram feed, I feel a strong inclination to replicate it.

Lately, I've been drawn to wearing stripes on stripes. This inspired me to pair patterned shorts with a striped polo shirt to create an eye-catching look. I finalized the ensemble with square-toe loafers and ivory ankle socks to maintain the preppy aesthetic and make the look infinitely more interesting than sneakers would.

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5

Nikki Chwatt wears a brown leather jacket, a beige tailored vest, brown striped shorts, and beige Koio loafers.

(Image credit: @nikki.chwatt)

History has proven that adding a distressed brown leather jacket to any ensemble effortlessly lends a touch of edgy and stylish flair. I experimented with layering it over a tailored vest and brown striped shorts. To incorporate a bit of French-girl style, I completed the look with beige loafers and gold hoop earrings.

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Associate Fashion Editor

Nikki Chwatt is an associate fashion editor based in New York City. She joined Who What Wear in 2024 after writing fashion, beauty, and lifestyle content for WWD, Well+Good, Editorialist, and more. With a passion for personal style and the creativity that comes with it, one of Chwatt's goals is to help others understand that there is no such thing as a “good” or “bad” style; it’s just about putting an outfit together that makes you feel confident in yourself. When she's not writing, you can find her taking a Pilates class, reading a powerful romance novel, or exploring a new wellness spot in Manhattan.