The Best Kendall Jenner Style Moments

Including red carpet looks and plenty of off-duty outfits.

This article was originally published on August 21, 2023 and has been updated.

Growing up on reality television and living most of her life in the public eye, Kendall Jenner has had her fair share of viral moments — and attention-grabbing fashion looks — over the years. And we’re always on Kendall Jenner style watch.

As one of the world’s most well-known nepo babies-turned-supermodels, Jenner has honed her own unique style uniform. From her show-stopping Met Gala moments to her expertly curated street style looks, the Calvin Klein and L’Oréal ambassador has certainly carved out a space in the fashion world that sets her apart from her famous sisters.

In honour of Kendall Jenner’s ever-evolving sense of style, here are some of the top model’s best looks.

April 2024

Jenner took a sweet, almost traditional approach to Easter, celebrating with her famous family in a pretty white dress with black ribbon detailing from Rodarte.

March 2024

For a day of errands, the supermodel went for quiet luxury with a pop of colour, pairing a belted blazer and wide leg trousers with a tangerine shoulder bag from Bottega Veneta.

September 2023

Kendall pulled out the polish to attend The Row’s Spring 2024 presentation at Paris Fashion Week, tucking a trench-like blouse into a slim black midi-skirt. The model, who appeared on the legendary supermodel-heavy Versace runway in Milan alongside Claudia Schiffer, accessorized the look with her current favourite loafers and a top handle handbag from (who else?) Mary-Kate and Ashley Olsen’s fashion brand The Row.

For a rainy September day in New York, Kendall wore a butter yellow coat over a simple grey T-shirt and black tailored slacks. For her elevated dreary day look, Jenner added slim tortoiseshell sunglasses, a supple oversized black purse and classic black pumps.

No pants, no problem! Kenny went XL with her shirt and handbag and XXS (or non-existent, who’s to say?) with her shorts for a casual outing in NYC earlier this month. The model opted for an easy updo and simple jewellery to accent the leg-forward look.

August 2023

To attend a party for her 818 Tequila brand, Jenner stepped out in a sexy Gucci dress from the brand’s Fall 2023 collection. She paired the one-shoulder look with nude lingerie, slingback pumps and a Gucci shoulder bag that brought out the subtle shades of green in the dress’s sheer fabric.

While out and about in Los Angeles, Jenner channelled the California sunshine in this vibrant off-duty look. Jenner paired a bright yellow mini-dress from COS with a pair of classic black shades and completed the look with the Suzanne Small shoulder bag from Saint Laurent by Anthony Vaccarello.

June 2023

It was all about the accessories with this effortlessly cool look that Jenner sported while out and about in New York City’s East Village. The model upgraded the classic T-shirt and straight-leg jeans outfit with a pair of Gucci sunnies, leather loafers from The Row, a brown vintage Hermès Kelly and matching skinny belt.

@kendalljennerBottega twice a day♬ Bad b activated – Savage X Fenty

While on a trip to Paris, Jenner modelled not one, but two Bottega Veneta looks for TikTok. The first look featured the brand’s sophisticated cotton midi-dress with a keyhole cutout. Perhaps utilizing the now-viral “wrong shoe theory,” Jenner made the chic look infinitely most interesting by opting for a classic menswear loafer from The Row instead of a sexy heel. Then, she slipped on a yellow sequined mini-dress that was quintessential Kendall Jenner style.

As creative director of the brand, Jenner wore a monochromatic look while hosting the FWRD pop-up grand opening in Los Angeles. The pearlescent white outfit featured a one-shoulder top and miniskirt set by Rick Owens paired with a white, half-moon leather bag from The Row and Yeezy heels.

May 2023

While soaking up the sun on a beach holiday in the south of France, Jenner sported a breezy vacation look that screamed model off-duty. Wearing a sheer AMI Paris maxi-dress as a bikini cover-up, she completed the look with a Bottega Veneta tote bag, Gentle Monster sunglasses and flip flops from The Row.

Who could forget this Met Gala after-party look? To celebrate after the big fashion event, Jenner wore a Nensi Dojaka playsuit inspired by a look from Chanel’s Spring 1994 collection. The sheer look, which featured a fully exposed high-cut thong, was complemented by strappy Gianvito Rossi stilettos, a silver clutch, and simple stud earrings.

For one of their first public outings, Jenner wore a white tank top and brown miniskirt to a basketball game with Bad Bunny. While all eyes were initially on the rumoured couple, Jenner’s snakeskin boots by Gianmarco Lorenzi definitely stole the show.

April 2023

During a night out with her Bad Bunny, Jenner chose a unique look that has been best described as a nod to the “avant apocalypse” aesthetic. The outfit included a see-through Paloma Wool top and a baguette handbag, but the real star of the look was a toss-up between the Blumarine’s Fall 2023 collection mini-skirt and knee-high boots.

Not one to shy away from the sheer dressing trend, Jenner sported another transparent look to attend an event honouring Karl Lagerfeld in New York City just days before the Met Gala. The royal blue Alexandre Vauthier couture gown featured a mock neckline and a glamorous feathered skirt, not to mention a drop-waist silhouette that made the 5-foot-10-inch model appear even taller.

March 2023

Jenner stunned at the Vanity Fair Oscar party in a vintage Jean Paul Gaultier dress from the brand’s Spring 2008 haute couture collection. The look didn’t include any jewellery and Jenner wore a chic updo that allow the beauty of the bronzed gold gown with petal-like details to shine.

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