Kylie Jenner is not-so-secretly obsessed with Halloween. She’s known to hold a flash sale for Kylie Cosmetics on the spooky holiday (hello freebies!) and her costumes are always over-the-top, but in the best way.
The Lip Kit-creator is no stranger to a sexy costume — in fact, that’s definitely her thing. In 2015, the star dressed in an all-white ensemble consisting of an itty-bitty skirt, fur boots and a tiny top with a hood. But one of our favorite looks of all time is when she slayed as a Victoria’s Secret Angel in barely-there, sheer jeweled tights, a beige bra and massive angel wings.
The Keeping Up With the Kardashians star brought her A-game in 2019, blessing her 149 million Instagram followers with a handful of different looks for various parties and events. The beauty guru nearly broke Instagram when she dressed as a “grown up” Little Mermaid, donning a sexy ensemble complete with a long red wig, a seashell bra, a sequined green skirt with a thigh-high slit and the most adorable Flounder-inspired clutch.
But that’s not all! She dressed up as a Playboy Bunny for a Halloween party hosted by her close friend Anastasia “Stassie” Karanikolaou — which makes sense since the 22-year-old recently posed nude in her very own magazine spread. And just a few days earlier, the pair recreated Britney Spears and Madonna’s 2003 MTV Video Music Awards looks — and it was obviously iconic.
Scroll through for a look at Jenner’s best Halloween costumes of all time for outfit inspiration and a major dose of sexiness.