Tomboy Style, Now & Then: Inspired by Katharine Hepburn

Take one peek at the street-style scene, and it’s hard to ignore that menswear-inspired looks are trending in a big way. But the truth is, they have never really gone out of fashion. And for that, we have Katharine Hepburn to thank. Pioneering the borrowed-from-the-boys vibe long before it was a thing, she taught us, “If you obey all the rules, you miss all the fun.”

Leading by example, she favored boyfriend trousers, blazers, and loafers, much like the trendsetters of today. The key to recreating her iconic look? A rebellious attitude and the five pieces below.

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  1. Printed Tote: With a black plaid print, this boxy leather carryall nods to the American sportswear aesthetic, which Katharine was said to inspire.
  2. Leather-Strap Watch: Unlike the traditional bracelet style, this more masculine timepiece adds a touch of androgyny to any outfit.
  3. Embossed Moccasins: Behold, Hepburn’s go-to shoes. Take her cue and wear them peeking out from under roomy pants.
  4. Cashmere Sweater: Layered beneath a blazer or tucked into trousers, this super-soft turtleneck could have been plucked from Katharine’s closet.
  5. Wide-Leg Trouser: As her signature piece, these flowing pants helped pave the way for women everywhere to ditch their dresses and sport an unconventional look.

Take a cue from this rule breaker.

By Elizabeth Burns, Associate Fashion Editor

Images via Alfred Eisenstaedt/The LIFE Picture Collection/Getty Images; Archive Photos/Stringer/Moviepix/Getty Images; Mondadori/Mondadori Portfolio/Getty Images.