We see her sauntering down runways and in **Phil Oh’**s captivating street snaps, looking confident and at ease in her clothes and with herself. She’s the tomboy, and these days this gamine, rather than the va-va-voom vixen or the ladylike uptown girl, is front and center fashionwise.

And she’s hardly a new invention: The word tomboy dates to the late 1500s, when it was used to describe a bold-spirited or immodest woman. Fashionably speaking, the tomboy came of age in the Roaring Twenties, a time of great liberation for women in every way, including dress. The Jazz Age gave birth to the garçonne—a word referring both to the sporty, bob-haired look that women adopted, and a specific type of dress (described at the time by Vogue as being “good for the woman who wishes to look trim and boyish. It is as simple as its name implies, straight in line, one-piece, beltless.”) Coco Chanel—whose incredible success was due in large part to her sartorial borrowings from the men in her life: lovers like the horse-mad Boy Capel, the jewel-loving Grand Duke Dmitri, and the tweedy Duke of Westminister—was the epitome of the cropped-haired, independent, garçonne.

Throughout the twentieth century, the tomboy resurfaced, though the concept shifted with the times, from the preppy-athletic New England Katharine Hepburn in the 1940s to the alligator-wrestling, free-spirited style of **Lauren Hutton’**s 70s shoots.

By 2010, the tomboy look had evolved into a uniform—lived-in T-shirt, skinny jean, fitted jacket, and boots—with such immediate city-cool appeal that Alexander Wang told Vogue that model off-duty “is a term I use for developing my aesthetic.”

Enter 2014, with the likes of Daria Werbowy and Aymeline Valade taking cues from decades and muses past and ushering in a slightly tailored take on the style, subbing a Chanel-cardigan jacket for a leather biker, say, or a crisp cotton button-down for a jersey tee. Mixing up those tenets elevates the look, while keeping it surprising and fresh, and of course, a little rebellious—tomboys, after all, just want to have fun.+++large