Kendall Jenner Reveals Why Her Sisters “Side Eye” Her Fashion Choices

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It looks like Kendall Jenner doesn’t have to worry about her sisters borrowing her clothes. 

The supermodel admitted that her sisters – Kylie Jenner, Kim Kardashian, Khloe Kardashian, and Kourtney Kardashian – don’t always love her fashion choices.

Kendall Jenner shared in a recent Vogue video that her fashion sense sometimes stands out from her family. She explained that she occasionally gets curious—and slightly questioning—looks when she attends family dinners, with relatives asking about her unique outfits.

Honestly, as someone who’s built a brand from the ground up, I’ve learned not to worry about what others think. The founder of 818 Tequila feels the same way – she truly doesn’t concern herself with whether people approve of her style choices, and frankly, that’s incredibly empowering! It’s about owning your look and feeling good in your own skin.

“When I love something,” she said, “I love something.”

One item in her closet she really adores? Her carefully curated collection of Hermès bags. 

Kendall explained that she’s very careful with her Hermès bags, especially the vintage ones, which she particularly loves.

She highlighted a favorite Hermès Kelly bag, explaining that she loves its well-worn look. She specifically mentioned the aged, slightly cracked leather, and even the scratches and scuffs – she appreciates all the signs of wear and tear, even on the corners.

She added, “This is so chic to me and so beautiful.”

When asked about her style, Kendall Jenner explained that comfort is the most important thing for her when choosing what to wear.

You know, I’ve always believed that feeling good in your own skin is the key to everything. And honestly? It’s true! When I’m comfortable – really comfortable – that’s when I feel my happiest, and, well, my most confident too. It’s a total game-changer, and it really does translate to how you carry yourself.

She developed that perspective over time. Kendall remembered feeling quite differently when she was younger.

I used to wear really high heels—huge ones—with everything,” the 30-year-old explained. “I actually used to believe the shoes were what completed the look.”

Kendall quipped, “That is so not the case for me anymore.” 

To look back on some of Kendall’s best fashion looks, keep reading. 

Kendall Jenner kicked off the 2025 Vogue World fashion show by modeling a memorable outfit – the iconic costume Nicole Kidman wore in the 2001 movie, Moulin Rouge!

The reality star stunned in a flowing white dress at the L’Oréal Paris fashion show during Paris Fashion Week in 2025.

For the 2025 Met Gala, she wore a suited look by Torishéju Dumi.

Kendall attended the 2025 Vanity Fair Oscar After-Party in archival vintage Mugler.

I was absolutely floored when I saw Kenny at the Academy Museum Gala! She completely transformed her look, swapping her usual brunette hair for a gorgeous blonde style. And that dress – a stunning Schiaparelli Haute Couture gown – was just incredible. She really turned heads!

She showed her support for Team USA at the 2024 Olympics in Paris.

Kendall dazzled in an archival Givenchy gown by the late Alexander McQueen at the 2024 Met Gala.

The model deserved her own trophy for her Maison Margiela look at the 2024 Vanity Fair Oscar Party.

Kendall picked a fiery Fendi gown for the 2023 Annual Academy Museum Gala. 

Kendall put a modern spin on the classic little black dress, choosing a daring David Koma design with a see-through top and vibrant red floral details covering the chest.

Everyone was watching Kendall at the 2023 Vanity Fair Oscars after-party, where she stunned in a dress by Jean Paul Gaultier.

She was shining bright at the 2023 Met Gala in a pantless Marc Jacobs bodysuit.

Kenny turned heads at the Nobu Dubai opening in 2023 with a vibrant chartreuse dress and striking, long latex gloves.

The reality TV star, known from The Kardashians, wore a cheerful floral dress and boots to the Marni Spring 2023 fashion show, accompanied by her boyfriend at the time, Devin Booker.

At the 2022 Vanity Fair Oscar Party, Kendall stunned in a black Balenciaga gown, finishing the look with her vibrant red hair.

Kendall contrasted her dark Prada gown at the 2022 Met Gala with strikingly bleached blonde eyebrows.

At the 2022 event celebrating The Kardashians, the founder of 818 Tequila made a statement, wearing a Givenchy outfit with shoes from the Yeezy brand, signaling her serious approach to business and fashion.

In 2021, she showed off her style by confidently wearing a striking black and white patterned crop top and pants.

Oh my gosh, did you SEE her at the Met Gala?! She was absolutely breathtaking! I mean, completely covered – head to toe – in jewels, and that Givenchy gown? Forget about it! It was a total moment, seriously. I’ve been replaying the pictures in my head all day!

Kendall brought culottes into the 21st century with this leather look in 2020.

Kendall rocked a sparkly neon green bodysuit to the 2020 Brit Awards.

She turned heads at the 2019 Emmys wearing a striking floral gown by Richard Quinn. The dress had a bold touch with its latex top and sleeves.

I was absolutely obsessed with Kendall’s look at the 2019 Cannes Gala! She wore this gorgeous pink dress from the Giambattista Valli collaboration with H&M, and it was just stunning on her.

Kendall knew how to mix business with fashion in this blazer and matching heels in 2019.

Kendall stole the show at the 2019 Met Gala in this orange feather dress by Versace.

Kendall attended the launch party for Chaos SixtyNine Issue 2 in London, where she was photographed smiling. She wore a spring 2019 dress by Dudas and PVC Season 6 shoes from Yeezy.

In 2019, Kendall Jenner attended a Los Angeles Lakers game and was seen wearing leather pants with Yeezy heels.

The model stunned in a LPA Aurora dress and Yeezy heels at Revolve’s 2018 #REVOLVEawards.

I was totally obsessed with Kendall’s outfit at the Kardashian-West Christmas Eve party! She wore this gorgeous off-the-shoulder gown, and it was designed by Christian Siriano – so chic!

Kendall was rolling in a green coat in New York City over her birthday weekend in 2018.

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2026-02-28 02:18