Revisiting Kylie Jenner’s Most Memorable Fashion Moments, From King Kylie to Front Row

Rise and shine: it’s Kylie Jenner’s 29th birthday! Over the 18-plus years since she launched into reality show fame, we’ve watched Jenner grow up before our very eyes, from spunky youngest child on Keeping Up With the Kardashians to fashion week front row fixture. Now, as she’s transformed from a kid to a mother herself, Jenner has tried just about every look under the sun.

In the earliest days of her fame, Jenner was wont to wear bold colors and loud prints (see: the coordinating neon pink and zebra outfits she and Kendall wore to Wango Tango in 2008). But over time, an edgier sense of style emerged, largely influenced by the Tumblr-era soft grunge moment. Perhaps her most iconic look of all time (dare I say!), she arrived at the 2014 Billboard Music Awards, hair shorn into a turquoise ombré bob, crowning herself “King Kylie.”

A few years later, Jenner began to dip her toe into high fashion. She attended her first-ever Met Gala in 2016, dressed in a glittering Balmain dress by Olivier Rousteing. The following year, she walked the carpet alongside Donatella Versace.

In recent years, though, Jenner has leaned all the way into fashion. Perhaps nothing is more exemplary than her arrival at the Schiaparelli spring 2023 couture show, an enormous faux lion’s head sitting atop her bust. She even flipped the script, trading in the front row seat to close Coperni’s Disneyland Paris show last year. But while she’s deadly serious about turning a look, Jenner approaches her style with a sense of humor, best exemplified by the custom fluorescent orange Chrome Hearts dress she wore to match beau Timothée Chalamet at his Marty Supreme premiere.

Here, we revisit Kylie Jenner’s most memorable fashion moments, from zebra and tulle to her latest custom Schiaparelli Met Gala dress.