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5. Alexander McQueen, from under $1,000
British-born Lee Alexander McQueen CBE was a designer at Givenchy from 1996 until 2001 and became the chief designer there quite rapidly. He went out on his own in 1992 and his sneakers, pumps, sandals, and boots are recognizable from the Punk and Wander styles to Oversized Sneakers, Tread Slick, and Deck Plimsoll designs. McQueen had a background in tailoring before venturing into fashion design and shoes and had a controversial business relationship with Gucci in 2000. He eventually extended to perfume, accessories, eyewear and…menswear! McQueen designed 36 womenswear collections in his lifetime and had celebrity clients like Lady Gaga, the Duchess of Cambridge, Michelle Obama, and Drew Barrymore. He sadly died by suicide in 2010, aged 40.