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Kendall Jenner's Best Outfits Throughout the Years

Kendall Jenner's Best Outfits Throughout the Years

By Janaya Holmes

Updated Aug 20, 2020 @ 12:12 pm

Credit: 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, Kendall Jenner knows how to make an entrance. Take a walk down memory lane with Kendall's best looks ever.

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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!

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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.

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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.

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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.

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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.

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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.

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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.

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Baby’s First Met Gala

The epitome of glamor! Kendall stunned in a Topshop mermaid gown, champagne clutch, and diamond necklace at the Metropolitan Museum of Art Costume Institute Gala, "Charles James: Beyond Fashion," in 2014.

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In Olcay Gulsen

The brunette posed in a Olcay Gulsen backless, cut-out halter top and pleated sequined pants at the 2014 Billboard Music Awards, for which Kendall was a presenter.

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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.

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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.

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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.

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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.

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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.

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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.

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Green Goddess

Perhaps one of the model’s most memorable looks, Jenner’s embellished Calvin Klein gown reigned supreme at the "China: Through The Looking Glass" Costume Institute Benefit Gala at the Metropolitan Museum of Art. The dress included a sophisticated mock neck and long laced tassels at the sides.

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Courtside Cameo

If there’s one take-away 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.

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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.

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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, a diamond necklace and matching bracelet.

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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.

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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.

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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 that, according to her Instagram post at the time, required a village, 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.

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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.

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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.

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Met Gala-Chic

Kendall attended her third Met Gala in an Atelier Versace cutout dress with a mirroring caged print. To compliment the serenity of the gown, she opted for natural-looking makeup and a sleek bun.

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Red Carpet-Ready

The model drew attention at the screening of From The Land Of The Moon (Mal De Pierres) at the annual 69th 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.

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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.

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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.

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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.

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Seeing Stars

While on a stroll in Paris, Kendall wore a revealing sheer turtleneck, star pasties, slim black pants and a color-blocking patchwork denim jacket with fur sleeves.

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More

Kendall Jenner's Best Outfits Throughout the Years

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Fashionable Beginnings

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It-Factor

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Budding Beauty

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Lady In Red

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Laid-Back and Edgy

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White Hot

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London Calling

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Baby’s First Met Gala

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In Olcay Gulsen

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Jaw-Dropping Slits

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Model Behavior

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In Octavio Carlin

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Sheer Sighting

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Belle of the Ball

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Facing the Music

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Green Goddess

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Courtside Cameo

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In Balmain

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When in Cannes

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Playful in Calvin Klein

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Pretty In Pink

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Laced Up Lady

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Airport Attire

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In Vivienne Westwood

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Met Gala-Chic

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Red Carpet-Ready