Vogue September cover girl Kendall Jenner is one of the world’s most recognizable faces—treading the line between modern supermodel, original beauty vanguard, and Instagram savant as effortlessly as breathing. Each day, she invites her 63 million followers to enjoy up-to-the-minute aesthetic updates, detailing everything from power naps to poolside hangs. And yet true Jenner-ites know there’s nothing that thrills her more than a little shock value—the kind that serves up an iconoclastic dose of selfie-fueled mischief.
There have been bold hair transformations—think raven-rooted pink and near-blanched trompe l’oeil wigs shared with a mysterious emoji or quippy phrase—and provocative body-con reveals. From Jenner’s brief brush with blue eyes to her untiring efforts to #freethenipple, here are our favorite fearless Insta-beauty moments.
COTTON-CANDY PINK HAIR
While Jenner
s raven mane functions as an above-the-neck calling card, the model has been known to test-drive cheekier tones. This trompe l’oeil hairpiece (posted during downtime on a Vogue shoot) is youthful, irreverent, and surprisingly fresh.
BODY-CON BELFIES
“If you’ve got it, flaunt it” summarizes Jenner’s free-spirited philosophy when it comes to body confidence. The model has been known to turn her back on the camera to show off the flip-side of her killer jeans—and the fruits of a well-honed workout.
THE BLUE STEEL REVEAL
Jenner temporarily traded her signature doe-eyed gaze for a set of icy blue–color contacts, a look she augmented with a cool-toned metallic makeup palette and the requisite supermodel smize.
NEXT-LEVEL LEG EXPOSURE
The red carpet, to-the-hip slit may have been reintroduced by Angelina Jolie Pitt, but Jenner’s literal waist-grazing variations—showcasing shoes, legs, thighs, and a swath of pelvic bone—have paved the way for a new era of delightfully scandalous glamour.
BLONDE AMBITIONS Before her stint as a blonde on Balmain’s Fall 2016 runway—for which she and BFF Gigi Hadid, among others, took twinning beauty to new heights—Jenner toed sunnier waters with a bedtime selfie featuring a golden, Barbie-esque wig.
PLAYFUL PIERCINGS
While her famous piercing has since been well-documented, Jenner first revealed her new body art on Instagram, followed shortly thereafter with a lineup of #freethenipple street style moments that require their own opus.
Kendall Jenner gets a big Kardashian family surprise to celebrate her Vogue cover:
Save
Save
