It’s hard to open a fashion magazine or celebrity rag this year without reading tomboy-this or boyfriend cut-that. Twenty years ago, however, or even five, the word tomboy, both as a noun and an adjective, was—let’s face it—as outré as “girl power” is today. In fact, throughout the twentieth century, the mass marketing of gender stereotypes—Barbie being the perfect example—meant tomboys cropped up in only small numbers against the odds, trends, and ads. Not so anymore: casual menswear-infused fashions for women have positively exploded into the mainstream under the helm of designers and stylists ranging from J. Crew to Rag & Bone, creating a mass acceptance of both the word tomboy and the women associated with it.

We’re not just talking style—it’s important to understand that being a tomboy isn’t something you can accomplish by wearing a pair of your boyfriend’s Levi’s down Robertson Boulevard. It goes far beyond fashion. True tomboys are measured in equal parts wardrobe and spirit. They are adventurous, confident, independent, rebellious, and ballsy. Katharine Hepburn, perhaps the tomboy of all tomboys, famously told Barbara Walters in 1981, “I’ve just done what I’ve damn well wanted to and I’ve made enough money to support myself and I ain’t afraid of being alone.” This from the woman who wore pants at a time when it was a serious sartorial crime for women to do so. Indeed, if it weren’t for Hepburn, who also breathed life into the onscreen tomboy of all tomboys, Jo Marsh of Louisa May Alcott’s Little Women, those basking in the gleam of how damn cool it is to wear plaid and rock the fedora wouldn’t be doing so today.

And where Hepburn epitomized the cross-section of tomboy look and spirit, Marlene Dietrich used it to expand society’s definition of feminity. She sauntered around Paris in a man’s tuxedo some 80 years ago. Far from suggesting male or transvestite traits, she reset the bar for women while still being sought after by men. In fact, seminal macho man John Wayne called Dietrich “the most intriguing woman I’ve ever known.”

Today the gamut of true contemporary tomboys runs wide—socialites, actresses, rockers, and models all want in on the action. But only those who take their queues from the legends and simultaneously embody the look and soul of the tomboy can actually pull it off. Witness Vogue fashion icon and writer Lesley M. M. Blume, who recently wore a Dietrich-inspired tailored tux to the Frick Ball in New York City. “I’ve rarely felt as glamorous… I doubt the most elaborate Oscar de la Renta ballgown could have had the same effect. I can’t explain the calm of it, sailing around in tails amidst a sea of satin dresses. And yet, it still felt distinctly feminine”€”albeit a stranger, more extravagant version of femininity,” she told TomboyStyle.

Kristen Stewart, the anti-starlet of the Twilight saga is also unfussy and sexy—and just headlined the film The Runaways as iconic rocker Joan Jett, who once said “I grew up in a world that told girls they couldn’t play rock ‘n’ roll.” Ditto British model Agyness Deyn, who cut her hair short when she was only 13, then became a skinhead when she was 17.

Yes, today even the word itself—which society used to employ pejoratively—has taken on aspirational meaning. Not only are girls and women embracing the idea of the tomboy, but they’re reaching for it, even the unlikeliest of them all, Paris Hilton, has proclaimed she is one. Undoubtedly, as society ventures into deeper definitions of style and femininity, so too the tomboy will evolve.

Then again both fashion and tomboys are known for their fleeting personalities.

Photo of Lesley M. M. Blume by Katie Fischer.