(Source: Instagram/@kimkardashian)
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22. Kim Kardashian as Anna Wintour
Kim Kardashian, North West, Kim's bestie/makeup artist Joyce Bonelli, and Joyce's son took the fashion world by storm by dressing up as some of fashion's most influential names in for Halloween in 2014. North was Vogue editor Andre Leon Talley, Joyce was Voque creative director Grace Coddington, Joyce's son was Karl Lagerfeld, and Kim was Anna Wintour, of course.

Image here.