Revisit Birthday Girl Kendall Jenner's Most Jaw-Dropping Fashion Moments Ever

Kendall Jenner officially turned 27 years old on Nov. 3, and we're celebrating by taking a look back at her best looks over the years, from memorable Met Gala ensembles to sheer gowns and more.

By Paige Strout Nov 03, 2022 12:00 PMTags
Watch: See ALL of Kendall Jenner's Show-Stopping Fashion Looks

The first week of November is full of Kardashian-Jenner birthdays.

Kendall Jenner officially turned 27 years old on Nov. 3, just two days before her mom Kris Jenner's birthday on Nov. 5. Having gone from being a reality TV star to one of the biggest supermodels in the world, Kendall's fashion evolution proves just how far she's come over the years.

Kendall—who is currently dating NBA player Devin Booker—began establishing herself as a red carpet staple in the early 2010s, wearing looks by designers such as Fausto Puglisi, Emilio Pucci and Calvin Klein at awards shows, premieres and film festivals.

And the more her modeling career took off, the more she experimented with her style, from rocking faux bangs at the 2015 American Music Awards to her black, sheer 2016 Cannes gown to her iconic orange feathered Met Gala ensemble in 2019.

Flash forward to 2022, and she's become a total trendsetter, wearing everything from slip dresses to fun prints and even bleaching her eyebrows for the 2022 Met Gala.

photos
Kendall Jenner and Devin Booker: Romance Rewind

In celebration of the birthday girl, scroll below to take a look back at Kendall's most jaw-dropping looks ever.

Floral Explosion

Kendall redefined the little black dress with this sexy David Koma number that featured a completely sheer and bright red petal pasties.

Gold Goddess

All eyes were on Kendall at the Vanity Fair Oscars party.

No Pants, No Problem

The supermodel shined bright at the 2023 Met Gala in a pantless Marc Jacobs bodysuit.

Bright and Bold

The 27-year-old dazzled in a bright chartreuse dress paired with latex leather opera-length gloves. 

Flower Power

The Kardashians star sported a fun, floral dress and boots while attending the Marni Spring 2023 with her then-BF Devin Booker.

Hollywood Glam

Kendall looked like a movie star in her black Balenciaga gown at the 2022 Vanity Fair Oscar Party, and completed the look with her new red locks.

Green With Envy

This green slip-on dress has us feeling envious of Kendall's wardrobe.

Bleached Brows

Kendall balanced her the darkness of her 2022 Met Gala ballgown by Prada by bleaching her eyebrows blonde.

Black & White

Kendall proved she can rock the boldest of patterns in this matching black and white crop top and pants.

Business Chic

Kendall showed she means business at the FYC Event for The Kardashians, pairing her Givenchy outfit with shoes by Yeezy.

Cool Culottes

The supermodel brings culottes into the 21st century with this leather look.

Bejeweled

Kendall was covered head-to-toe in jewels in her 2021 Met Gala gown by Givenchy.

Neon Dream

Kendall dons a sparkly neon green bodysuit to the Brit Awards.

Coming Up Roses

Kendall attended the 2019 Emmys in a statement-making floral gown featuring an edgy latex top and sleeves.

Kotton Kandy

Kendall looks extra sweet in this pink gown at the Cannes Gala.

Let's Get to Werk!

The supermodel knows how to mix business with fashion in this blazer and matching heels.

Oh, La La!

Kendall stole the show at the Met Gala in this orange feather dress by Versace.

Always Looking Bright

Kendall posed and smiled at the Chaos SixtyNine Issue 2 launch party in London and wore a Dudas Spring 2019 dress and Yeezy PVC Season 6 shoes.

Basketball Beauty

Kendall smiles as she sits courtside at a Los Angeles Lakers game wearing leather pants and Yeezy heels.

Fangirl for Feathers

The model looked fantastic in a LPA Aurora dress and Yeezy heels at Revolve's second annual #REVOLVEawards.

Off the Shoulder & Off the Charts

Kendall got festive at the Kardashian-West Christmas Eve party in an off-the-shoulder gown designed by Christian Siriano

Go Green

The 25-year-old flashed a huge smile as she rode a Citi Bike in a green coat in New York City over her birthday weekend.

All That Glitters Is Gold

Kendall shocked with her sheer gold Julian Macdonald look at the 2018 British Fashion Awards.

Level Up

Kendall took flare pants and long sleeves to a whole new level in this all-black Vera Wang ensemble.

Cute in Corsets

The model made a case for corset-bearing dresses and trendy tinted sunglasses.

Perfect in White

Shutting down the Met once again, Jenner stuns in this heavenly Off-White number. 

Queen of Sheer

Looking like a ruffled goddess, Jenner came to slay, princess-style, in this white, sheer, layered gown. 

Barely There

We're sure all eyes were on Kendall at the Met Gala when she arrived in this La Perla slip. 

Couture Queen

The model let it all follow behind her in this glamours Giambattista Valli Couture dress paired with white heels. 

Smart Casual

The Jenner sister decided to spark things up wearing this over-the-top Alexandre Vauthier piece with a plain pair of jean shorts and pumps. What a combo. 

photos
View More Photos From Kendall Jenner's Best Looks
Can't keep up? Get every update, exclusive clips and more from your favorite family.