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’s black sweatshirt is by Cherry LA.
Kendall Jenner’s green tie-dye sweatshirt is by Good American; her leggings are from Alo Yoga.
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’s multi-colored sweater vest is from Mango, her trousers are from Aritzia, and her handbag is from Burberry.
Kendall Jenner wears an oversized white button-down shirt with pleated trousers from The Row.
Kendall Jenner wears a cream cardigan with black stitching from Korean label The Open Product.
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 wears a long navy blue coat with white stitching, paired with loose-fit stonewashed jeans, and Prada loafers.
Kendall Jenner’s beige waistcoat-as-a-top look is straight out of the early-90s Melrose Place era in fashion.
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.
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 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 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.
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 pairs an oversized black blazer with leather-look trousers.
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 pairs a St. Agni slip dress with black-and-red cowboy boots
Balmy summer nights in France call for midriff-baring Jacquemus.
Kendall Jenner was photographed in New York during fashion week in a body-con strapless little black dress.
Kendall Jenner dresses up a minimalist halter top and miniskirt with chunky platform ankle boots.
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.
