There's a self-assured nonchalance that comes with rejecting the way your gender is 'supposed' to dress and borrowing your style from the opposite sex. It's the act of a woman who knows her mind. In other words, tomboys are cool – they just are.

Of course these inspired women come in more than one form: there's a difference between the le smoking wearer in pin-sharp tailoring, and the scruffy young model in a hoodie and no make-up. But both are rejecting the idea of being overtly feminine – both are playing around with clothing conventions and confidently doing things their own way.

Dressing in androgynous or masculine clothing can be more comfortable and less constricting, as tomboy heroine Katharine Hepburn always insisted. But it's also just a little bit rebellious. With that in mind, let's celebrate the style of 16 women, from Coco Chanel to Cara Delevingne, who've done menswear better than the boys.

 

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