His Turns Hers

In 2026, a woman wearing pants is commonplace. Even sporting a tie barely bats an eye. This was not always the case, as women wearing menswear began as a revolutionary act.

As early as the 1850s, feminists Susan B. Anthony, Sarah Bernhardt, Amelia Bloomer, and Elizabeth Cady Stanton wore bloomers, trousers, and pantsuits, a revolutionary act against the restrictiveness of women’s clothing at the time.

In the 1920s, Coco Chanel became the true trailblazer for menswear in women’s fashion. The designer spotlighted suits, blazers, and trousers for an androgynous look that appeared on models and actresses, then the modern woman.

Dressy meets bossy with a 1990s Victoria’s Secret slip, vintage men’s Dior oversized blazer, and gold aviator sunglasses. (Photo by Alicia Osborne)

There remains a staying power to women donning menswear because of the juxtaposition. Boxy silhouettes against soft curves. A crisp button-down with flowing tulle. Baggy trousers styled with a fitted top.

We spoke with Lexi Angeles, owner of West Side Vintage in Pensacola, about the timelessness of menswear for women.

“Menswear for women withstands the test of time because many of those pieces have classic silhouettes that can be reinvented over and over again,” says Angeles. “I love that menswear gives women the freedom to play with proportions, mix masculine and feminine elements, and create outfits that feel natural and authentic to who they are.”

Sweetly Suited

Pinstripe pencil skirt by Aknvas with a white oversized button-down and Hermes crossbody tote (photo by Alicia Osborne)

Classic styling of menswear began with boxy blazers, tailored trousers, crisp shirts, and loafers.

“An oversized blazer, men’s trousers, or even a classic button-down can instantly elevate a look when paired with something a little softer,” says Angeles. “Throwing a blazer over a dress, cuffing the sleeves, and adding chunky jewelry can make the outfit feel effortless while still adding your own personality. I also love styling vintage men’s trousers with a fitted top and loafers to bring the whole look together.”

For an evening out, consider wearing an oversized button-down as a dress and pulling it together with either a chunky belt or men’s tie around the waist. Pair it with heels, and layer on the jewelry.

She Wears the Pants

Photo by Alicia Osborne

The wearing of pants was how women first started to revolutionize their wardrobes.

Trousers are wonderful for their versatility. Wear a well-tailored pair to the office with a puff-sleeve top, or for the weekend, try a pair a half-size bigger to hang off the hips with a tight white tee and eye-catching heels.

Jeans reign supreme. From bootcut to baggy to knee-length jorts, men’s jeans work as well on women.

“Baggy jeans let me breathe, and when you mix that relaxed fit with feminine pieces like kitten heels, a fitted blouse, or a fun top, it creates that effortless cool girl look,” says Angeles. “It’s that balance of feeling comfortable while still feeling dressed up that I love.”

In warmer months, Angeles loves a pair of men’s denim cutoff shorts. She describes a cool vintage graphic tee with denim cutoffs and boots as her daily uniform.

Sporty Spice

Photo by Alireza Mirzabegi U Fmlscwnzq via Unsplash

Since the ’80s, sportswear as everyday wear has been trending. Think stylish sneakers, luxe tracksuits, cute baseball hats, hoodies, oversized sweatshirts, and jerseys.

“I grew up with two older brothers, and most of my hand-me-downs included baseball jerseys and oversized graphic tees,” says Angeles. “A vintage graphic tee is one of those pieces that never stops being cool. It tells a story, adds personality to an outfit, and can be styled a hundred different ways.”

For fall and winter, Angeles finds herself reaching for a cozy crewneck. Select a unique color like a deep plum, emerald, or burnt orange, and style it with jeans and loafers, or pull it over a dress with combat boots.

With many sports gearing up in the fall, consider a jersey paired with a patterned skirt, track pants with a cropped tank top, or vintage sneakers with a floaty peasant dress.

Finding Your Fit 

Photo by Christophe Dusabe Vuqhjovhcom via Unsplash

As a vintage store, Angeles loves helping customers dig through the treasure trove of the store to find a timeless piece to add to their wardrobe that can be styled many ways.

“For me, the best menswear pieces are the ones you actually want to wear over and over again,” says Angeles. “They’re comfortable, versatile, and become a part of your everyday style.”