40 and Fabulous: Fashion Rule Breakers

This year marks W’s 40th anniversary. To celebrate, we take a look back at the boldest and bravest style makers who have appeared on our pages. Click here to purchase *W: The First Forty Years*.
Whether sporting a sequin-encrusted body stocking or a feather-festooned costume during her Half-Breed album phase, the original pop provocateur has never been afraid of walking on fashion’s wild side.
Somehow, the Nicaraguan bombshell made every outfit—from a man’s pantsuit to a bohemian frock (like the one, above, far left, she wore to Michael and Tina Chow’s wedding)—look immensely sexy.
Speaking of Tina… With her gamine hairstyle and proclivity for simple, clean-lined clothes, the late model and jewelry designer became a muse to the likes of Helmut Newton and Karl Lagerfeld, who credited her with inventing minimal chic.
Decades after she hit the scene with her flattop ’do and high-def style, Grace Jones is still influencing fashion—not to mention today’s pop stars, who continually mine her sartorial repertoire, which includes this majestic Issey Miyake look.
From her early punk bondage gear to her recent political-slogan tees, Vivienne Westwood has stood as the grande dame of subversive English fashion for over 30 years.
She’s always known how to shock an audience. Here she models Jean Paul Gaultier—her way.
The erstwhile Filipino First Lady might have been stripped of her power but never of her butterfly-sleeve dresses, which were as much a symbol of her reign as her 3,000 pairs of shoes were.
Before she wore raw meat and rode around in an enormous egg, Gaga was just a girl in ugly jeans and a pretty Miu Miu jacket.