Celebrity Kendall Jenner's Best Outfits Throughout the Years From the streets of NYC to Hollywood's red carpet. By Janaya Holmes Updated on February 24, 2023 @ 10:20AM Pin Share Tweet Email Photo: Getty Images Kendall Jenner went from reality star to top model in just a few years. Within that time we've seen her on red carpets, backstage at fashion shows, and all over the town (namely at Nobu), wearing some of the most coveted looks from the top designers. From her standout street style to her red-carpet glam, Jenner knows how to make an entrance. Take a walk down memory lane with Kendall Jenner's best looks ever. 01 of 41 Fashionable Beginnings Kendall Jenner arrived at the 8th Annual Teen Vogue Young Hollywood party wearing a crisp white blouse with structured sleeves, complete with an adorable, yet sophisticated bow. The starlet fancied a jade green wrap skirt and patent leather lace-up oxfords, perfect for dancing the night away. 02 of 41 It-Factor Draped in a plunging pastel blouse and cascading tresses, Jenner attended the 2011 Hollywood Style Awards in West Hollywood. Her white peplum skirt was secured with a silver metallic belt, accompanied by an enviable pair of cuffed chrome heels. 03 of 41 Budding Beauty The young television personality nailed down her poses even before making it big as an internationally-known supermodel. In 2012, Kendall attended the premiere of The Hunger Games in a becoming printed sheath dress. 04 of 41 Lady In Red The brunette turned heads in a keyhole-accented crimson gown with embellished cap sleeves at The Heart Truth's Red Dress Collection Fall 2013 Mercedes-Benz Fashion Show. 05 of 41 Laid-Back and Edgy Jenner traded her traditional red carpet style for a more casual look. The reality star chose a loose-fitting graphic tank, chic leather leggings and studded stilettos at 102.7 KIIS FM's Wango Tango event. 06 of 41 White Hot Kendall attended the 2013 American Music Awards in an edgy asymmetric co-ord look. Jenner donned metallic accessories and a bold red lip for a pop of color. 07 of 41 London Calling In the early stages of her career, soon after gaining undeniable fame as a model, Kendall graced her success with great strides. In 2016, the household name was seen attending a show during London Fashion Week in an all-black look that screamed sleek and chic. 08 of 41 Baby's First Met Gala The epitome of glamor, Kendall stunned in a Topshop mermaid gown, champagne clutch, and diamond necklace at the 2014 Met Gala, "Charles James: Beyond Fashion." 09 of 41 In Olcay Gulsen The brunette posed in an Olcay Gulsen backless, cut-out halter top and pleated sequined pants at the 2014 Billboard Music Awards, for which Kendall was a presenter. 10 of 41 Jaw-Dropping Slits Kendall arrived at the MuchMusic Video Awards in a regal Fausto Puglisi gown, complete with statement jewels and daring slits. Kendall and her sister, Kylie, served as hosts for the 2014 award show in Toronto, Canada. 11 of 41 Model Behavior The model struck a pose in an olive green utilitarian Balmain piece while attending the Vogue Foundation Gala as part of Paris Fashion Week at Palais Galliera. 12 of 41 In Octavio Carlin Jenner exuded an ethereal essence at the 2014 Harper's Bazaar ICONS Celebration. The beauty floated along the carpet in a romantic Octavio Carlin cream satin gown with a floor-grazing train. She topped off the look with a slick updo and deep red lip. 13 of 41 Sheer Sighting The eldest of the Jenner sisters stood tall in a show-stopping halter mesh gown adorned with geometric panels on the 2014 American Music Awards red carpet. 14 of 41 Belle of the Ball Kendall attended the 2015 amfAR New York Gala in a stunning Romona Keveza red one-shoulder gown, accompanied by sparkly stilettos and a Harry Winston tennis bracelet. 15 of 41 Facing the Music What better way to embrace music festival season than with long cut-off denim shorts, a suede leather vest, and a fringe purse? Jenner rocked snakeskin booties, a print bikini top, and layered jewelry at the 2015 Coachella Music Festival. 16 of 41 Green Goddess Perhaps one of the model's most memorable looks, Jenner's embellished Calvin Klein gown reigned supreme at the 2015 Met Gala, "China: Through The Looking Glass." The dress included a sophisticated mock neck and long laced tassels at the sides. 17 of 41 Courtside Cameo If there's one takeaway from this outfit, it's the knee-high boots. Kendall gave an understated crop top, denim shorts, and a structured coat an elevated edge with these towering gladiator boots. 18 of 41 In Balmain Kendall opted for an androgynous aesthetic at the 2015 Billboard Music Awards. The star donned a velvet Balmain blazer, hand-crafted with pearls, along with thigh-high black boots and a volume-defying hairdo. 19 of 41 When in Cannes In May 2015, the model made one of many appearances during the 68th Cannes Film Festival, at the premiere of the film Youth. Looking sun-kissed and poised, Kendall wore a two-piece lace ensemble complete with a diamond necklace and matching bracelet. 20 of 41 Playful in Calvin Klein Kendall arrived at amfAR's 22nd Cinema Against AIDS Gala in a purple cut-out Calvin Klein dress. Jenner twirled the grounds in Cap d'Antibes, France looking effortlessly gorgeous. Her fresh piecey updo and flowy skirt epitomized the effervescence of spring. 21 of 41 Pretty In Pink The supermodel gave her best Blue Steel pose at the world premiere of Zoolander 2 in New York City. Jenner embraced a rather simplistic look compared to her more adventurous attire as she strutted the carpet in a rose pink satin A-line dress and white pumps. 22 of 41 Laced Up Lady Balancing elements of femininity and avant-garde punk just right is an art form Kendall Jenner champions in the utmost effortless manner. Standing tall in lace-up DSquared2 heels, Jenner attended the 2016 MTV Movie Awards. Her Kristian Aadnevik dress with lace details, reminiscent of her heels, was cinched at the waist with a studded belt. 23 of 41 Airport Attire If you thought combining comfort and style was impossible, this photo of Kendall Jenner's airport outfit has just proven you wrong. While Kendall chose this matching camel and burgundy tracksuit for the tarmac, her versatile co-ord is suitable for running errands, meeting up with friends, and more. 24 of 41 In Vivienne Westwood Jenner, who was the subject of a few playful jokes during the annual White House Correspondents' Dinner, engaged in the good-natured humor with grace while wearing a strapless Vivienne Westwood gown, a radiant Lorraine Schwartz choker, and Dolce and Gabbana sandals. 25 of 41 Met Gala-Chic Kendall attended her third Met Gala in an Atelier Versace cutout dress with a mirroring caged print. To complement the serenity of the gown, she opted for natural-looking makeup and a sleek bun. 26 of 41 Red Carpet-Ready The model drew attention at the screening of From The Land Of The Moon (Mal De Pierres) at the 69th Annual Cannes Film Festival. Jenner amazed in a long sleeve sheer gown embellished with a winding snake print. The barely-there dress included black high-waisted briefs for coverage. She also sported a pair of cascading statement earrings, accenting the glittering details of her dress. 27 of 41 In Elie Saab The celebrity invoked boudoir chicness in Elie Saab couture. While in Cannes, Kendall attended the 2016 Chopard Party garbed in a floral minidress topped with a matching floor-length robe, decorated with feathered sleeve details. 28 of 41 Birthday Behavior Towering in her crystalline heels, the star celebrated her 21st birthday in an outfit that paid homage to a 2000s-era Paris Hilton. Kendall shimmered in a custom LaBourjoisie chain dress cloaked in Swarovski crystals while stepping into her 20s-themed party. 29 of 41 Off-Duty Style Kendall hit the streets of L.A. in a basic white tee topped with a lace bralette and printed velvet robe. She kept it cool and casual in light-washed ripped jeans, ankle boots, and round, oversized glasses. 30 of 41 Winter Wonderland En route to the a/w 2017: Love Me 17 X Burberry party at Annabel's, Jenner draped herself in a cozy oversized knit sweater over a simple beige dress. She highlighted her wardrobe with chocolate brown eyeshadow, bold red lips, and her signature middle part. 31 of 41 Barely There Kendall Jenner is no stranger to daring looks, and arguably the most audacious of all was this backless La Perla dress. The slip included a dramatic cut-out, exposing her chiseled core and torso. From behind, a mere thong and ruched fabric for coverage. Leaving little to the imagination, the lace bodysuit proved sensual, yet fashion-forward, and the shimmering sheer details on the draping slip showcased true elegance. 32 of 41 Taking Flight In true camp fashion, the supermodel went over the top in a festive orange Versace dress. Complementing her sister Kylie's lavender get-up, Kendall's gown also included awe-inspiring feathers. Kendall's orange diamond jewelry and face-framing tendrils added a touch more drama. 33 of 41 La Vie En Rose Kendall Jenner was a vision as she attended the 2019 amfAR Cannes Gala in this dreamy bubblegum pink Giambattista Valli. The strapless gown draped layers and layers of tulle and cinched at the waist with an adorable bow — a dress fit for a princess. Jenner exuded regality while roaming Hotel du Cap-Eden-Roc. Her dark brown hair delightfully contrasted the bright shade of the dress, while her rose-mirrored sandals accented it. 34 of 41 90s Throwback Channeling major 90s Princess Diana vibes, Kendall was seen out in NYC sporting a structured black blazer over a similar-hued graphic tee and turtleneck. Her mom jeans loosely tucked into a pair of chunky combat boots, Jenner's outfit rendered new-age business casual attire. 35 of 41 Blondes Have More Fun While out in Milan during Fashion Week Spring/Summer 2020, Kendall revealed a newly dyed hair color, polished into a neat bun. The model clutched a black baguette purse while hitting the streets of Italy in a chained halter top and matching zebra print pants. 36 of 41 Out Of This World Kendall attended The Box BRIT Awards 2020 afterparty in London wearing a futuristic Saks Potts glitter long-sleeve top and matching pants. She finished the look with a charming high ponytail, silver metallic bag, and transparent, crystal-adorned Amina Muaddi heels. 37 of 41 Vest as Shirt Raymond Hall / GC Images The off-duty model was seen stepping out in NYC's midtown wearing high-waisted trousers and a black and white floral vest sans shirt. 38 of 41 Sheer Bodysuit Axelle / Bauer-Griffin / FilmMagic At the 11th Annual LACMA Art + Film Gala, Jenner stunned in a sheer black Burc Akyol bodysuit and draped silver skirt. 39 of 41 Urban Cowgirl The LA native bundled up while on the east coast in this shearling jacket and mashup of brown suede and denim jeans. 40 of 41 Hello, Moto Rachpoot / Bauer-Griffin / GC Images With her racing jacket and blue jeans, Jenner's street-style game is on point. By swapping out a classic leather jacket for this Nascar one instead, she gives the model off-duty uniform a slight twist. 41 of 41 Dubai Bling Kevin Mazur / Getty Images While in Dubai for the opening weekend of Atlantis The Royal, Jenner was the picture of luxury. She wore a Schiaparelli black satin dress with a gold chain halter and neckline complete with molded lips because... why not?