Kendall Jenner’s Cozy Winter Looks: From NYC Sneakers to Parisian Boots

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In March 2015, Kendall Jenner showcased her signature blend of edgy yet comfortable style while braving the cold temperatures and snow in New York City. True to her philosophy—“I guess my style’s a little edgy but comfortable. I like being comfortable, for sure, and kind of casual”—she paired a chic Proenza Schouler sweater with black trainers for a cozy yet fashionable look.

The following day, she carried the same effortlessly cool outfit to Paris but elevated it with sleek over-the-knee boots, proving her ability to transform a single ensemble with the right footwear.

Cozy and Chic in NYC: Kendall Jenner’s Proenza Schouler Sweater and Black Trainers

Kendall Jenner braves the cold in a Proenza Schouler color-block sweater, pairing cozy style with effortless sophisticationKendall Jenner braves the cold in a Proenza Schouler color-block sweater, pairing cozy style with effortless sophistication

In the Big Apple, the then-19-year-old American fashion model and reality television personality styled her Proenza Schouler color-block sweater and “Gettin Hi Skinny” by RES Denim pants with a fashionable pair of black trainers. She carried a “Medium Lucrezia Duffel” by Givenchy.

Kendall Jenner paired a Proenza Schouler color-block cashmere sweater with RES Denim Gettin Hi the Shining pants, Puma Modern Court high-tops, a Givenchy Lucrezia bag, and Fendi Karlito and pompom bag charms in snowy New York City on March 3, 2015Kendall Jenner paired a Proenza Schouler color-block cashmere sweater with RES Denim Gettin Hi the Shining pants, Puma Modern Court high-tops, a Givenchy Lucrezia bag, and Fendi Karlito and pompom bag charms in snowy New York City on March 3, 2015

Kendall Jenner’s fashion choices often highlight her affinity for stylish sneakers, seamlessly blending comfort with high fashion. For instance, during a casual outing, she paired a chic ensemble with the classic Adidas ‘Stan Smith’ sneakers, showcasing her ability to elevate everyday footwear into a fashion statement.

In another instance, Kendall was spotted at LAX sporting Balenciaga ‘Race Runner’ sneakers, effortlessly combining a Vetements tracksuit with these sleek kicks for a sporty yet chic airport look. Additionally, her collaboration with Jimmy Choo’s Fall 2022 campaign featured a range of footwear, including off-duty sneakers, highlighting her versatility in styling both casual and high-end pieces.

Sophisticated in Paris: Kendall Jenner Elevates Her Look with Over-the-Knee Boots

Kendall Jenner stuns with effortlessly tousled waves, natural makeup, and a striking gaze that perfectly complements her chic Proenza Schouler ensembleKendall Jenner stuns with effortlessly tousled waves, natural makeup, and a striking gaze that perfectly complements her chic Proenza Schouler ensemble

Arriving in the French capital for fashion week, Kendall Jenner swapped her trainers for a pair of over-the-knee “Dae” boots from Alice + Olivia, adding a touch of sophistication to her Proenza Schouler ensemble.

Reflecting on her influences, Kendall once shared, “My style icon actually is my three sisters. I love the way they dress and the way they put things together. I definitely get most of my style from them.” This familial inspiration shines through as she effortlessly balances bold and elegant elements in her looks.

Kendall Jenner styled a Proenza Schouler color-block cashmere sweater with black leather over-the-knee boots and a Celine Nano bag in Paris on March 4, 2015Kendall Jenner styled a Proenza Schouler color-block cashmere sweater with black leather over-the-knee boots and a Celine Nano bag in Paris on March 4, 2015

Kendall Jenner’s Effortless Style with Knee-High Boots

Kendall Jenner consistently showcases her flair for incorporating knee-high boots into her ensembles, effortlessly blending sophistication with a modern edge. Notably, during the Jimmy Choo Fall 2022 campaign, she donned the striking Blake Metallic 110mm Wedge Boots, crafted from gold liquid metal leather, which added a bold statement to her look.

n another instance, Kendall was spotted at Renell Medrano’s NYFW exhibit wearing Alexander Wang’s Mascha stretch-vinyl knee boots, featuring a sleek square toe and chunky high heel, perfectly complementing her vintage-inspired outfit. Additionally, she embraced a utilitarian aesthetic with Prada’s Monolith mini bag knee-high boots, known for their distinctive detachable zipped pouches, adding a functional yet stylish twist to her streetwear ensemble.

Do you prefer her black sneakers or the over-the-knee boots with this ensemble? If you’re looking for a new pair of boots, you can find similar styles from a variety of footwear designers at Zappos.

Luxe, soft stretch leather composes these Tamara Mellon thigh-high boots, yielding a sleek, second-skin fit through the shaftLuxe, soft stretch leather composes these Tamara Mellon thigh-high boots, yielding a sleek, second-skin fit through the shaft

Explore Kendall Jenner’s Iconic Style Moments

Kendall Jenner’s fashion evolution continues to captivate, seamlessly blending comfort with high fashion. Her recent appearance at Gucci’s Spring/Summer 2024 Milan Fashion Week show, alongside Bad Bunny, showcased her ability to make bold statements.

For those interested in her off-duty style, Kendall’s collaboration with Jimmy Choo’s Fall 2022 campaign highlighted her versatility in footwear choices. Additionally, her daring ‘naked dress’ at the LACMA Art + Film Gala exemplified her fearless approach to fashion.

These instances underscore Kendall’s dynamic presence in fashion, continually setting trends and inspiring enthusiasts.