Katharine Hepburn’s assertive and independent personality permeated all aspects of her life, from the witty and intelligent characters she played on screen to her rebellious, androgynous style. The Oscar-winning actress dared to wear masculine-inspired clothing at a time when her fellow starlets were sporting ultra-feminine, sex-kitten ensembles. But it worked, Katherine’s boyish style ensured she stood out from the crowd and paved the way for androgynous dressing throughout the decades. Countless celebrities, from Janelle Monae to Emma Watson, often shun a glamorous gown for a sleek tux at award bashes. There’s a key to nailing this look however, team your tux with sleek, retro waves to soften the style. Extra points for sporting a light auburn, red hair colour, a la Katharine.