Kendall Jenner Best Outfits 2021
Kendall Jenner’s best outfits of 2021 (photos: Getty Images)

Model and reality TV star Kendall Jenner may be best known for her high-fashion runway work and coterie of glamorous sisters and friends—but some of Jenner’s best looks of 2021 were spotted on the streets of New York City and Los Angeles, as Jenner was going about her everyday life. From morning gym sessions to daytime dates and black-tie formalwear, Jenner is a fashion chameleon whose personal style reflects a strong sense of SoCal identity as well as great eye for proportion and color. Here are some of Jenner’s best outfits of the year. Which is your favorite?

Kendall Jenner wears Monochrome Athleisure

Whether she’s working out or just hanging out, Jenner is a fan of monochrome athleisure outfits. In early 2021, Jenner was photographed out and about in Los Angeles wearing the trendy look—paired with Yeezy’s often-copied “Pure” slides and Adidas’ all-white Ultra Boost sneakers.

Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – FEBRUARY 1: Kendall Jenner is seen on February 1, 2021 in Los Angeles, California. (Photo by Rachpoot/MEGA/GC Images)

Kendall Jenner’s black sweatshirt is by Cherry LA.

Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – FEBRUARY 27: Kendall Jenner is seen on February 27, 2021 in Los Angeles, California. (Photo by Rachpoot/MEGA/GC Images)
Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – MARCH 10: Kendall Jenner is seen on March 10, 2021 in Los Angeles, California. (Photo by Bellocqimages/Bauer-Griffin/GC Images) *** Local Caption *** Kendall Jenner

Kendall Jenner’s green tie-dye sweatshirt is by Good American; her leggings are from Alo Yoga.

Kendall Jenner Best Outfits 2021
LOS ANGELES CA – APRIL 7: Kendall Jenner going to pilates on April 7, 2021 in Los Angeles, California. (Photo by Crown Media/MEGA/GC Images)

Is Kendall Jenner… Preppy?

While Kendall Jenner and her sisters—Kylie Jenner and the Kardashian trio—are probably best-known for their glamazon aesthetic, some of Kendall’s best (and most relatable) street style looks this year have veered into preppy territory. In her down time, she seems to favor comfy sweater vests, cute boxy cardigans, tailored white button-down shirts, and casual trousers—often paired with chunky loafers.

Kendall Jenner Best Outfits 2021
NEW YORK, NY – MARCH 21: Kendall Jenner is seen on March 21, 2021 in New York, New York. (Photo by MEGA/GC Images)

Kendall Jenner’s multi-colored sweater vest is from Mango, her trousers are from Aritzia, and her handbag is from Burberry.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – APRIL 27: Kendall Jenner is seen in Tribeca on April 27, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner wears an oversized white button-down shirt with pleated trousers from The Row.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – APRIL 27: Kendall Jenner is seen in Tribeca on April 27, 2021 in New York City. (Photo by Gotham/GC Images)
Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – APRIL 24: Kendall Jenner is seen in SoHo on April 24, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner wears a cream cardigan with black stitching from Korean label The Open Product.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 11: Kendall Jenner is seen in Midtown on September 11, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner wears California casual

You can take a supermodel out of SoCal, but SoCal style will always be part of her DNA. When she’s not on the runways in Paris, Milan, and New York, Kendall Jenner is often photographed wearing California casual—a relaxed silhouette and a soft, muted color palette reminiscent of Melrose Place and Beverly Hills, 90210 (the original series).

Kendall Jenner Best Outfits 2021
NEW YORK, NY – MARCH 22: Kendall Jenner is seen on March 22, 2021 in New York City. (Photo by David Krieger/Bauer-Griffin/GC Images)

Kendall Jenner wears a long navy blue coat with white stitching, paired with loose-fit stonewashed jeans, and Prada loafers.

Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – MAY 26: Kendall Jenner is seen on May 26, 2021 in Los Angeles, California. (Photo by MEGA/GC Images)

Kendall Jenner’s beige waistcoat-as-a-top look is straight out of the early-90s Melrose Place era in fashion.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 12: Kendall Jenner is seen in SoHo on September 12, 2021 in New York City. (Photo by Gotham/GC Images)

An unstructured throw-on-over-a-tank-top cardigan—especially when paired with casual thong sandals and a baseball cap—is classic Southern California cool, even though this photo was snapped in SoHo, New York City.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 14: Kendall Jenner is seen on September 14, 2021 in New York City. (Photo by Gotham/GC Images)

A soft, cream over-shirt looks nearly-monochrome with loose-fit khakis and platform slides. Kendall Jenner wears this ’90s-inspired look well—paired with a deep, smoky eye and double face masks? It’s positively 2021.

Kendall Jenner Best Outfits 2021
NEW YORK, NY – OCTOBER 15: Kendall Jenner is seen on October 15, 2021 in New York City. (Photo by MediaPunch/Bauer-Griffin/GC Images)

Kendall Jenner wears a cropped black-and-white flower-motif sweater from Tach Clothing—and while the top is cut in a youthful, contemporary silhouette, its intarsia-inspired look feels like a throwback to cozy mom sweaters in the late-’80s.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – APRIL 28: Kendall Jenner is seen in Tribeca on April 28, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner wore a sunny head-to-ankle pastel yellow matching set—jacket and high-waisted trousers—from Meryll Rogge while out and about in New York this spring.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 10: Kendall Jenner is seen at the Michael Kors fashion show during New York Fashion Week at Tavern on the Green in Central Park on September 10, 2021 in New York City. (Photo by Gotham/GC Images)

A little white tank top, bell bottoms, and chunky black platform shoes was the uniform of the mid- to late-90s, and Kendall channels the era in this outfit, running between New York Fashion Week shows this past autumn.

Kendall Jenner and the case of the oversized tops

Mastering a street style look doesn’t have to be complicated—and Kendall Jenner has a natural eye for proportions and silhouette. One easy way to look effortlessly cool is to pair a structured oversized top or jacket with structured trousers or slim-fit leggings. Here are two of Kendall Jenner’s best street style looks in this category—one dressier, one less formal.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – APRIL 26: Kendall Jenner is seen in Tribeca on April 26, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner pairs an oversized black blazer with leather-look trousers.

Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – MAY 17: Kendall Jenner is seen promoting her line of Tequila, “818” on May 17, 2021 in Los Angeles, California. (Photo by Bellocqimages/Bauer-Griffin/GC Images)

Kendall Jenner wears a blue quilted vest from her own 818 Tequila merch line, paired with neat white jeans and Converse Chucks.

Kendall Jenner’s best going-out outfit ideas of 2021

Dressing up for going out is where the Kardashian-Jenner family really excel. At black tie events, like this year’s Met Gala, Kendall Jenner opted for a jaw-dropping over-the-topped bejeweled sheer gown—but when she dresses for casual evening outings, her personal style is far more minimalist. Check out some of Jenner’s best going-out looks of 2021.

Kendall Jenner Best Outfits 2021
LOS ANGELES, CA – MAY 27: Kendall Jenner is seen on May 27, 2021 in Los Angeles, California. (Photo by Bellocqimages/Bauer-Griffin/GC Images)

Kendall Jenner pairs a St. Agni slip dress with black-and-red cowboy boots

Kendall Jenner Best Outfits 2021
SAINT-DENIS, FRANCE – JUNE 30: Model Kendall Jenner attends the Jacquemus “La Montagne” show at La Cite Du Cinema on June 30, 2021 in Saint-Denis, France. (Photo by Marc Piasecki/Getty Images)

Balmy summer nights in France call for midriff-baring Jacquemus.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 09: Kendall Jenner wears a little black dress during New York Fashion Week on September 09, 2021 in New York City. (Photo by Gotham/GC Images)

Kendall Jenner was photographed in New York during fashion week in a body-con strapless little black dress.

Kendall Jenner Best Outfits 2021
NEW YORK, NEW YORK – SEPTEMBER 10: Kendall Jenner seen out and about in Manhattan on September 10, 2021 in New York City. (Photo by Robert Kamau/GC Images)

Kendall Jenner dresses up a minimalist halter top and miniskirt with chunky platform ankle boots.

Kendall Jenner Best Outfits 2021
NEW YORK CITY, NY – SEPTEMBER 10: Kendall Jenner heading to Zero Bond on September 10 2021 in New York City, New York. (Photo by MEGA/GC Images)

Kendall Jenner heads out to private members’ club Zero Bond in a chic little 1920s-inspired mini-dress by Saint Laurent.

And, last but certainly not least, Kendall Jenner’s stellar Givenchy Haute Couture ‘naked dress’ at this year’s Met Gala is absolutely, hands-down, the model’s best outfit of 2021.

Kendall Jenner Best Outfits 2021
US model Kendall Jenner arrives for the 2021 Met Gala at the Metropolitan Museum of Art on September 13, 2021 in New York. – This year’s Met Gala has a distinctively youthful imprint, hosted by singer Billie Eilish, actor Timothee Chalamet, poet Amanda Gorman and tennis star Naomi Osaka, none of them older than 25. The 2021 theme is “In America: A Lexicon of Fashion.” (Photo by Angela WEISS / AFP) (Photo by ANGELA WEISS/AFP via Getty Images)
thoughts?