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Kendall Jenner street style© Grosby Group

14 times Kendall Jenner made the streets her runway

From hitting the gym to going to dinner, the model always looks effortlessly chic.


Fabiana Buontempo
Senior Writer
UPDATED JANUARY 26, 2021 2:34 PM EST

It doesn’t come as a surprise that  Kendall Jenner  always looks chic and cool without trying too hard. The 25-year-old model always oozes confidence as she can simply throw on a crop top and leggings, and she looks fabulous. Jenner definitely has her own style which is a bit more casual compared to her famous sisters and we’re here for it.

Here are 14 times Jenner turned heads with her cool street style.

Kendall Jenner out in NYC© GrosbyGroup

Out for Dinner

The 25-year-old made the New York City streets her runway in a black head-to-toe The Row outfit. So chic and sophisticated!

Celebrity Sightings: February 20th - Milan Fashion Week Fall/Winter 2020-2021© GettyImages

Milan Fashion Week

Earlier this year during Milan Fashion Week, the model looked fashionable yet comfortable in a white top, black trouser pants, with a long black coat over it. She topped off her look with colorful sneakers.

Kendall Jenner and Bella Hadid in New York City© GrosbyGroup

New York City Trip

During a recent trip to Manhattan, Jenner wore a cream-colored turtleneck tucked into black trousers. She wore a long camel wool coat over it and kept her feet comfortable in Nike sneakers.

Kendall Jenner and Devin Booker© GrosbyGroup

Date Night

While out on a date night with rumored beau, Devin Booker, Jenner wore a simple and sexy outfit which consisted of a white crop top under a black leather jacket paired with black high-waisted jeans and a brown belt. She topped off her look with a brown purse and black boots.

Kendall Jenner and Hailey Bieber go on a shopping trip© GrosbyGroup

Shopping Trip

While on a casual shopping trip with BFF Hailey Bieber , Jenner kept things simple in a white crop top paired with high-waisted beige pants and heels.

Kendall Jenner© GrosbyGroup

Party Time

For a house party at Justin and Hailey Bieber ’s house a few months back, the 25-year-old model wore a silky cream-colored crop top paired with black high-waisted pants, and a purse on her shoulder.

kendall jenner and hailey bieber© GrosbyGroup

Grocery Store Run

Once again, the 25-year-old was seen with Hailey Bieber in an athleisure outfit that showed off Jenner’s toned abs.

Kendall Jenner out on a stroll© GrosbyGroup

Outside Stroll

For a stroll around her neighborhood, Jenner wore a blue short-sleeved shirt paired with black capri leggings. She carried a white tote bag on her shoulder and wore slider sandals on her feet.

Kendall Jenner out in LA© GrosbyGroup

Leaving the Gym

We can’t get enough of seeing the model in athleisure wear. Recently leaving a gym in LA, Jenner wore a lime green sports bra paired with black high-waisted workout pants and a cropped sporty jacket over the look.

Celebrity Sightings In New York City - February 24, 2020© GettyImages

Airport Attire

Jenner was seen arriving in New York City earlier this year in a comfy green sweater and black yoga pants. Talk about the perfect airplane attire!

Kendall Jenner street style© GrosbyGroup

Out in LA

Clearly, Jenner is a fan of showing off her model legs by wearing high-waisted pants. While out in LA, the 25-year-old wore a cropped beige sweater paired with white pants and bright orange sneakers. She accessorized with a Louis Vuitton shoulder bag.

Kendall Jenner in London© GrosbyGroup

Pre-COVID-19 Restrictions

Prior to all of the COVID-19 restrictions, Jenner was seen in London after a fashion show wearing a very bright lime green onesie that showcased her toned model physique.

Kendall Jenner leaving the gym© GrosbyGroup

Leaving the gym

Jenner is the queen of athleisure wear. Even leaving the gym, the supermodel looks fabulous and must we say not sweaty!

Kendall Jenner in Aspen© GrosbyGroup

Staying warm in Aspen

Jenner kept warm while in Aspen with her family in a grey cardigan layered over a brown turtleneck paired with black leggings, boots, and a long coat. Stylish yet warm!