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The Best Celebrity Halloween Costumes of All Time

Vogue Logo By Jenna Rennert of Vogue | Slide 1 of 21: The countdown is officially on: the spookiest night of the year is quickly approaching. While it’s tempting to keep things easy by picking up a pair of cat ears en route to the Monster Mash, why not plan ahead this October with a meticulously executed costume that's heavy on shock value? For inspiration, look no further than the most memorable guises of Hollywood's favorite faces. After all, these actresses, actors, singers and It-girls know how to make an entrance.
For a crime-fighting night out in New York City, beauty chameleon Rihanna and her crew once transformed into a trio of pizza-eating Ninja Turtles, courtesy of some masterfully applied green body paint. Serena Williams played to her inner nerd with a set of taped glasses and an off-center ponytail for an 80’s prom queen look worthy of the homecoming dance. Risk takers will relish Marc Jacobs' excessively contoured and eerily real female bodybuilder, perfected with French-tipped talons, a metallic blue bikini, and some jaw-dropping prosthetics.
From Cher’s epic Cleopatra recreation to Kylie Jenner's spot-on portrayal of Christina Aguilera—right down to her "Dirrty" string-threaded micro-braids and chaps—here are the best celebrity Halloween costumes of all time.

The countdown is officially on: the spookiest night of the year is quickly approaching. While it’s tempting to keep things easy by picking up a pair of cat ears en route to the Monster Mash, why not plan ahead this October with a meticulously executed costume that's heavy on shock value? For inspiration, look no further than the most memorable guises of Hollywood's favorite faces. After all, these actresses, actors, singers and It-girls know how to make an entrance.

For a crime-fighting night out in New York City, beauty chameleon Rihanna and her crew once transformed into a trio of pizza-eating Ninja Turtles, courtesy of some masterfully applied green body paint. Serena Williams played to her inner nerd with a set of taped glasses and an off-center ponytail for an 80’s prom queen look worthy of the homecoming dance. Risk takers will relish Marc Jacobs' excessively contoured and eerily real female bodybuilder, perfected with French-tipped talons, a metallic blue bikini, and some jaw-dropping prosthetics.

From Cher’s epic Cleopatra recreation to Kylie Jenner's spot-on portrayal of Christina Aguilera—right down to her "Dirrty" string-threaded micro-braids and chaps—here are the best celebrity Halloween costumes of all time.

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