Kendall Jenner's Best Style Moments

In the past few years, no one's style has garnered quite as much attention as Kendall Jenner's. The model has pioneered major trends from athleisure to naked dressing and everything in between. She's changed up her looks (and stylists), but no matter what she's in, Kendall is in command of the trends. And while she may have once been known as a younger sibling to her Kardashian sisters, she's carved a niche for herself that's led to turns down the runways of top design houses.

Kendall Jenner's off-the-runway style has caught our attention time and time again, but certain outfits remain favorites. Some are cool takes on everyday basics; others are eye-catching red carpet ensembles, but we consider all of these some of her best. She may be just 21, but Kendall has clearly set herself apart as a trendsetter in the fashion industry. So which outfits of Kendall's made the cut? Read on to see the most iconic Kendall Jenner styles!

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On Kendall Jenner: Jonathan Simkhai Pleated Combo Classic Pintuck Button Down Blouse; Adidas socks

We already know Emily Ratajkowski and Bella Hadid are fans of bike shorts, but Kendall Jenner just showed us how to try the trend for the airport. She upgraded the casual item with a button-down shirt that boasts on-trend statement sleeves, which is kind of genius if you ask us. The result? Business on top, party on the bottom. 


Try a Colorful Mini Dress
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On Kendall Jenner: Ralph Lauren Collection striped sequin mini-dress

Sequins for day: why not? Jenner wore the ultimate head-turning mini dress with tried-and-true white sneakers, and we want to recreate this look ASAP. While the dress's silhouette is simple, the rainbow colors take it to the next level. 


Do Basics Well
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On Kendall Jenner: Adidas Forum Lo Sneakers ($100); Louis Vuitton bag

High-waisted jeans, a comfy white tee, and sneakers are all part of the NYC uniform, but Kendall's handle on the details make all the difference. Her cool '90s-inspired sunglasses, Louis Vuitton bag, and Velcro-strap sneakers (which are currently on sale!) take basics to the next level.


Throw It Back
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On Kendall Jenner: Haider Ackermann Silk-Satin Shirt ($682); Danielle Guizio jeans; Céline shoes

Leave it to Kendall to make '80s-inspired pieces feel chic—her teal silk-satin pajama top looks modern and fresh when styled with a cropped tank, vintage jeans, and sleek white mules.


Tired of Boring Black Tights? Wear Brown Ones
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On Kendall Jenner: Prada bag

Instead of wearing her black bag and shoes with a pair of black tights (as one would expect), Jenner chose sheer brown ones, which made her shorts and oversize (also brown) sweater look even cooler, in our opinion. Anyone else contemplating buying a pair of brown tights now like we are?


Baggy is Chic
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On Kendall Jenner: Vera Wang Oversized Jacket ($3999); Saint Laurent Jodie Boots ($657)

Comfort enthusiasts, this one's for you: Turns out it is possible to wear several slightly oversize items at once. Here, Kendall leans into the play on proportion with straight-leg mom jeans and a soft hoodie made forward-thinking with a statement leather-and-shearling jacket.


Flaunt Your Fandom
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On Kendall Jenner: Topshop x Stranger Things hat; Balenciaga Raw Cut Hem Japanese Denim Jacket ($1250)

As it turns out, Kendall Jenner is not immune to Stranger Things mania. Grabbing dinner in L.A. with sister Kourtney Kardashian, she wore the Topshop x Stranger Things cap, which is sadly sold out. While the limited-edition collab may have flown off shelves, we're hanging on to our Stranger Things obsession for the foreseeable future.


Add a Smart Touch With a Blazer
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On Kendall Jenner: Dior blazer; Danielle Guizio custom jeans; Céline mules

Blazers are back in a big way for fall—literally. Styled with white shoes (another major trend) and vintage denim, the oversize look oozes model-off-duty vibes.


Put a New Twist on the Classics
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On Kendall Jenner: Balenciaga bag

While ankle boots and skinny jeans will always be a classic combination, try mixing things up by swapping in styles that feel a bit more fresh. Jeans with front slits or a bold pair of red boots feel especially on trend this season.


Swap Out Your Stan Smith Sneakers
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On Kendall Jenner: Adidas Pharrell Williams Tennis HU Monochrome Sneakers ($99)

If you rely on your Adidas Stan Smiths or Gazelles over and over again, it might be time to switch things up with a different pair from the brand. Kendall Jenner wore sneakers from Adidas's collaboration with Pharrell Williams, and now we're dying to get our hands on them. Just add high-waisted leggings, a see-through top, and a black triangle bra à la Jenner.


Prepare for Polka Dots
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On Kendall Jenner: Bec & Bridge Resort 18 dress; Bagatiba Gold-Filled Saint Mary Necklace ($152); Adidas Yeezy sneakers

Further proof that polka dots are going to be the must-have print next season. Take note from Jenner, and pair a statement polka-dot piece with simple sneakers for an unexpected daytime look this fall.


Choose Unexpected Footwear
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On Kendall Jenner: Zimmermann Resort 18 dress; Alexandre Vauthier boots; Bagatiba D2C Necklace ($188)

Instead of opting for a more summer-inclined shoe style—e.g., a strappy sandal or heel—Kendall paired her frilly Zimmermann mini with knee-high slouchy boots. In turn, the outfit was given a totally different, moodier spin—which proves that footwear can truly dictate the vibe of a look.


Give a Night-Out Top a Daytime Spin
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On Kendall Jenner: Bec & Bridge top; Stuart Weitzman boots; Roberi & Fraud sunglasses

If you usually reserve your sheer, floaty tops for nights on the town, Kendall Jenner just might have you rethinking that decision. The model gave a red ruffle-sleeved top a daytime spin by pairing it with high-waisted jeans and white statement boots. If going totally sheer isn't your thing, consider layering a nude cami or pretty lace bra underneath.


Make Your Classic Accessory Feel Fresh
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On Kendall Jenner: Enfants Riches Déprimés top; Alexander Wang Antonia Ankle Strap Sandals ($238); Louis Vuitton bag

Jenner loves an old-school—but always classic—Louis Vuitton bag. While this particular Alma style originally debuted in 1992, she makes it feel current with her straight-leg jeans, graphic tee, and sleek heels.


Try a '90s-Inspired Sneaker Look
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On Kendall Jenner: Monse Asymmetric Mid-Rise Tapered Jeans ($790); Adidas Yeezy Powerphase Calabasas Sneakers ($350)

Tired of wearing leggings with sneakers? Channel Jenner by wearing an oversize blazer over a crop top and mom jeans with white sneakers for a '90s-inspired look.


Vacation in Style
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On Kendall Jenner: Le Specs Liberation Aviator Sunglasses ($89); Chanel shirt; Solid & Striped The Tania Top in Cream ($88); Adidas Skateboarding Stan Smith Sneakers ($70)

Try something unexpected for a swimsuit cover-up, like a Hawaiian shirt.


Embrace Your Surroundings
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On Kendall Jenner: Lisa Marie Fernandez Colby High-Rise Bikini ($420); Le Specs The Last Lolita Cat-Eye Sunglasses ($77)

Kendall Jenner turned heads in Cannes wearing a chic high-waisted swimsuit with an oversize straw hat and cute cat-eye sunglasses.


Go Tonal
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On Kendall Jenner: Ahlem Concord Sunglasses in White Gold ($450); Sergio Hudson shirt and skirt; Balenciaga Metallic Edge Mini City Bag ($1595); Acne Studios boots

Kendall opted for a streamlined and chic look in head-to-toe pale pink.


Add a Pop of Color
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On Kendall Jenner: Gucci camisole and skirt; Dries Van Noten choker; Kenneth Cole Krystal Patent Leather Boots ($495)

Sleek black boots and a black miniskirt are staples in every woman's closet. The addition of a colorful tank instantly makes your simple basics feel new.


Swap Skinny Jeans for Flares
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On Kendall Jenner: Elizabeth and James McKinley Oval Acetate Sunglasses ($185); Local Authority T-shirt; Gucci Belt With Double G Buckle ($390); Stella McCartney The '70s Flare Jeans ($542); Louis Vuitton boots

While Kendall is no stranger to skinny jeans, the model proved that flared denim can look equally cool. Add a statement belt or bold coat to complete the ensemble.


Dress Down Your Trousers
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On Kendall Jenner: Kendall and Kylie Vivian Sunglasses ($100); KG Kurt Geiger Strut Mid Heel Ankle Boot in White ($210)

Trousers don't have to be just for the office. Styled with eye-catching white boots and a casual tee, these pants look great off-duty too.


Don't Fear Volume
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On Kendall Jenner: Giambattista Valli couture gown; Chopard jewelry

For a major red carpet moment (or just a black-tie affair), a daring dress is the way to go. Try a voluminous sleeve or a train, and you're sure to own the room.


Try Femleisure
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On Kendall Jenner: Gucci Cat-Eye Sunglasses ($415); Daisy Broderie Lace-Up Corset Dress ($380); Fendi Micro Peekaboo Light Pink Sheepskin Micro Bag ($1950); Stuart Weitzman The Cling Booties ($598)

There's no need to stick to one ultra-specific style. Try mixing and matching flirty and sporty pieces together instead.

Want more Kendall? Check out the 10-piece Kendall Jenner wardrobe.

Aemilia Madden