Tomboy style, a mix of masculine and feminine ways of dressing that encapsulates “confidence, rebelliousness, and adventure,” has been a staple of women’s fashion since the beginning of the 20th century. And the look is constantly being reinvented— from Vassar girls back-to-school shopping at the Brooks Brothers’ flagship in 1950s Manhattan to Patti Smith wearing her unmistakable black necktie while belting out “Gloria” on a gritty stage in the Village.

When successfully executed, tomboy style allows for mobility and freedom without sacrificing femininity or fashion—an apt balance for any woman navigating New York. In the early 20th century, Coco Chanel borrowed tweeds and sweaters belonging to the Duke of Westminster and invented sportswear for women. In the 1960s Yves Saint Laurent created the classic Le Smoking Jacket for women, and in the 1980s Ralph Lauren and Lacoste polo shirts became a must-have in closets of both genders.

Diane Keaton’s quirky-preppy Annie Hall wardrobe, designed in part by then-newcomer Ralph Lauren, won over many a New Yorker in the late 1970s, and the late fashion icon Carolyn Bessette Kennedy stunned in a crisp oversize white button-down instead of a gown to attend the Whitney’s annual black-tie gala in 1999. J.Crew’s Jenna Lyons has made her mark on this century’s tomboy style by firmly cementing the look into mainstream retail while consistently elevating the idea of classic American staples. All three became famous for carving out their own definition of what it means to dress like a woman. They pushed the boundaries of conformity and carefully toed their limits so the next generation could push the boundaries even further.

Now we are watching a new generation grow up in a post-feminist world, hardly blinking at the idea that a woman can wear men’s clothing. Tomboy style continues to be championed by a new generation of creative designers, including Madewell with its artfully deconstructed jeans, which could pair seamlessly with The Row’s Perch-Patch blazer and a pair of Mark McNairy saddle shoes for good measure. The plethora of street style darlings embracing the trend today have popularized it once again, most notably Garance Doré, Gaia Repossi, Alexa Chung, and Brooklyn’s Marina Muñoz, who is well known for her men’s haberdashery habit. Today, tomboy style has become far less a fashion statement and more of a true lifestyle, embraced in numbers unmatched in any other era.

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