Women of gender-bending inclination have plenty of role models. Diane Keaton in Annie Hall. Bianca Jagger's sharp white suits, or Tilda Swinton's androgynous good looks. Even as Jenna Lyons designs for women, she shops from the men's side of J.Crew. These ladies look cool, effortless, yet put-together, especially when they wear clothes by Paul Smith — the Sir of menswear-for-women — or Stella McCartney, who earned her tailoring stripes at the old boys clubs of Savile Row.
Now, as men have gotten more into style, it's easier than ever to borrow from the boys. The key to pulling the look off is often pure tailoring and proportion, paired with the great accessories women already love. Mango's sharp-shouldered overcoat can top any outfit with a classic effect, while a jewel-toned suit from Elizabeth and James has a Miu Miu vibe and a cropped pant that works for day. Meanwhile, a checked bomber jacket is a modern replacement for the stalwart shrunken blazer, and looks smart with a cropped plaid pant from See by Chloe and Alexander Wang's monk strap brogues in a pop color. For the seventies swagger of David Bowie or Mick Jagger, turn to Miu Miu's clashing striped collar and Valentino's shiny slip-ons. But should one miss the sweeter life, simply try Dries Van Noten's heeled loafers — after all, every good tomboy has a feminine side. For the full range, click ahead to see 25 ways to get this look.