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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
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.
Shop the look:
Nordstrom
Pull-On Poplin Shorts
Banana Republic
Timeless Trench Coat
2
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.
Shop the look:
Good American
Poplin Shorts
Lovers and Friends
Terra Vest
Ancient Greek Sandals x Lucy Williams
Andros Sandals
3
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.
Shop the look:
J.Crew
Wren Slim Western Chambray Shirt
Sam Edelman
Kasey Square Toe Pumps
4
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.
Shop the look:
PARKE
Striped Boxer Shorts
Vagabond Shoemakers
Alex Penny Loafers
Éterne
Classic Rib Socks
5
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.
Shop the look:
Veronica Beard
Elbe Shorts
Gap
Linen-Cotton Halter Vest
Found
Leather Pocket Jacket
Shop more pajama-inspired shorts:
H&M
Cotton Boxer-Style Shorts
Less than $20? I’ll take two pairs, please.
THE FRANKIE SHOP
Lui Striped Twill Shorts
The Frankie Shop always knows what it’s doing.
Almina Concept
Boxer Cotton Shorts
American Eagle
Striped Boxer Shorts
According to Google Trends, shoppers are searching for American Eagle’s women’s boxer shorts.
Open Edit
Vacation Shorts
These have a sporty appeal that is so on-trend right now.
MORE TO COME
Amalie Relaxed Shorts
I love the shorter iteration of the trend.
The L.A.-based brand is known for its effortlessly cool West Coast style.
I proudly own this pair. The shorts fit so well and are so cute with a button-down shirt.
J.Crew
End-on-End Cotton Boxer Shorts
If stripes aren’t your thing, grab this solid-colored style.
Helsa
Wide Stripe Poplin House Shorts
Take style notes from Elsa Hosk and pair these with ankle socks, loafers, a cropped tee, and a headscarf.
