3. Anna Wintour
Anna Wintour? Repeating an outfit? It seems absolutely impossible – the Vogue superstar has access to a literally humongous closet fully stocked with the latest fashions at all times. However, even she isn’t immune to repeating an outfit if she likes it enough. She wore a floral Lanvin dress to a Moet & Chandon event in New York City, which she went to accompanied by their brand ambassador Roger Federer. She then took the dress across the world and donned it at a Yves Saint Laurent show during Paris Fashion Week, a little over a month later. If it works, it works – she definitely knows.