Audrey Hepburn

Audrey Hepburn was the picture of pared-down elegance both on and off screen. Who can forget the belted menswear button-down worn with a long skirt and flat sandals by Princess Ann in Roman Holiday? Or Jo Stockton’s Capri pants and ballet flats in Funny Face (revived years later by Gap for a TV ad). Or, of course, Holly Golightly's oversize sunglasses and little black dress in Breakfast at Tiffany's. At a time when curves ruled (Marilyn Monroe, Elizabeth Taylor et al.), Hepburn was the physical antithesis—gamine features, a slender boyish physique and a graceful gait born of years of ballet training. Her style choices were always about comfortable, casual elegance, not sex appeal.

Signature items: Black Capri pants, ballet flats, trench coats, turtlenecks, men's button downs