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 rebellion against the restrictiveness of women’s clothing.

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. 

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 Michelle Torregrosa, owner of Divas & Devils House of Style, about the timelessness of menswear for women. 

“At Divas & Devils, our focus is not on what’s trending, which is why we love menswear,” says Torregrosa. “Menswear for women is something we’ve always carried and always will.”

Photo by Alicia Osborne

The Art of the Blazer 

Torregrosa is quick to recommend a blazer as a staple piece in a woman’s wardrobe. 

Where women’s blazers tend to be overly tailored, Torregrosa prefers the oversized fit of a men’s blazer on a woman. She thinks the boxy fit pairs best with fitted or feminine pieces. 

“My personal opinion, and style, is to pair menswear with something ultra-feminine or sexy,” says Torregrosa. “Think a men’s oversized blazer with a slip dress or a floor-length tulle maxi dress.” 

Photo by Alicia Osborne

She Wears the Pants

Like blazers, Torregrosa likes to style men’s trousers on women for their contrasting fit and silhouette. 

“Men’s bodies tend to be squarer where typically women have curves, causing pieces like trousers to fit completely differently,” says Torregrosa. 

Torregrosa recommends women try a trouser in a half size too big, to hang off the hips. For the office, she suggests trousers with a fitted puff sleeve top. For an evening out: trousers, a tight white tank, and eye-catching stilettos. 

“I hardly wear jeans anymore because trousers are so transitional, yet elevated,” says Torregrosa. “I often encourage customers to try them because they can go from the office to a night out.” 

Photo by Alicia Osborne

Finely Coated 

In the fall and winter, a statement jacket or staple coat are pieces you will consistently reach for. Torregrosa advises a men’s bomber jacket, biker jacket, trench coat, or car coat as your top layer. 

“Most of the winterwear looks you see women wearing in magazines or on runways are actually men’s coats or jackets,” says Torregrosa. 

Belt or button a trench or car coat for a structured look with fitted trousers. Or, if long enough, wear it as a dress with heels. Leave it open over a slinky midi-dress or a mini-skirt and knee-high boots. 

Bombers or biker jackets are particularly versatile with a pair of trousers or a mid-length skirt for the office. Or, pair with jeans, a T-shirt, and combat boots for weekend wear. 

Photo by Alicia Osborne

Admirable Accessories 

Tie any outfit together with a tie. 

“Unexpected and sexy, wear a tie with a tube top,” says Torregrosa. “Or unbutton a button-down to the third button and leave the tie hanging.”

She also encourages wearing ties as belts or even bracelets. 

“A woman in men’s loafers is always chic,” says Torregrosa. “I always have a pair in my closet and always will.” 

Loafers are a multifaceted piece of menswear; try them styled with trousers and a tucked-in button-down or a babydoll dress. And that’s just the beginning.

Jewelry-wise, Torregrosa stocks and sells a considerable amount of menswear-inspired baubles such as chunky rings, chains, and vintage watches. Aviator sunglasses were originally worn by male pilots but now are a sunglass style that is flattering to most face shapes. 

Sporty Spice

While Torregrosa doesn’t keep much sportswear or athleisure in store, she notes that both began as styles typically reserved for men. Torregrosa’s spin on the look is one of her son’s hoodies and a pair of sleek sneakers paired with a voluminous tulle skirt. 

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. 

Photo by Alicia Osborne

Finding Your Fit 

As a vintage and designer store that is piece-driven rather than brand-driven, Torregrosa delights in being able to help customers find a timeless, key piece, be it a trench or trousers that they can style in a plethora of ways. 

“I bring customers a variety of looks, so they can get ideas on how to style and wear pieces,” says Torregrosa. “I educate on how to wear a piece by dressing it up or down, to work or for a night out, in summer or winter, and all the occasions in between.”  

Feature image by Alicia Osborne