The Piece: Originally out of Westwood's Spring/Summer 1984 Hypnos collection (see below), this jersey top is inspired by synthetic sportswear and merges her trademark bondage accents, courtesy of ribbed paneling, with a sleek, athletic feel. Available now for $900.
The Background: When she opened her boutique at 430 King's Road in London, Vivienne Westwood was one of the first designers who didn't just seamlessly bring fashion and music together, she regarded clothes as something more than what you wore. The store's first incarnation was Let It Rock ('50s-inspired Teddy Boy garb), and from there it evolved into Seditionaries ("specialists in rubberwear, glamourwear, and stagewear") and eventually SEX (the Sex Pistols would not exist if it weren't for the SEX shop), among others.
Bondage shirts, Mountain hats (thanks, Pharrell!), Pirate boots: From Malcolm McLaren, Westwood's one-time boyfriend and business partner, and Johnny Rotten to Chrissie Hynde (who worked the register at one time) to Siouxsie Sioux and beyond, you wore Westwood's pieces only if you identified with her rebellious, street-seasoned, music-fueled way of life. Needless to say, posers need not apply. "I always wanted to cut a dash," she has said. She's sliced and slashed more than that, to say the least.