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Anna Wintour: The Devil Wears Bob

July 21, 2025·1h 15m

Anna Wintour is one of the most famous ice queens, and one of the most powerful figures in fashion with her trademark bob and ever-present dark sunglasses. We take you through her rise to Vogue editor-in-chief in 1988 and beyond. Plus, we get into the juiciest rumors: did she really hook up with Bob Marley? Throw on your shades and cut your hair into a c*nty bob, we’re talking all things Anna! Groundbreaking.