Dave and Chuck The Freak

Kendall Jenner attends the 2023 Vanity Fair Oscar Party Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California.

It is no surprise that Kendall Jenner, being a Kardashian and supermodel, has become a fashion icon. Kendall constantly updates her Instagram page with flicks of her best outfits, and we are here for it! The 818 Tequila founder began modeling at age 13 when Wilhelmina Models signed her in 2009. Jenner switched to homeschooling to pursue her modeling career. After numerous magazine covers and runway walks, she moved on to more high fashion work, signing with The Society Management in 2013. Under the agency, she booked Marc Jacobs, Givenchy, Chanel, Tommy Hilfiger, Fendi, Bottega Veneta, and Dolce & Gabbana in her first year. Kendall is five-foot-eleven inches tall.

In 2015, Kenny walked in the Victoria’s Secret Fashion Show along with other notable luxury fashion brands. She then made Forbes magazine’s 2015 list of top-earning models, ranking at number 16 with an estimated annual income of $4 million. Two years later, she was named the world’s highest-paid model by the publication, beating Gisele Bündchen, who held the title for more than 14 years since 2002. She was making $22 million at this point.

Trouble with Clothing Lines

Besides modeling, Kendall and her younger sister Kylie Jenner had their own line with PacSun in 2012. The Kendall & Kylie Collection moved to Topshop three years later. In June 2017, the sisters launched a controversial line of “vintage” T-shirts on their website for their brand, Kendall + Kylie. Retailing at $125, the “Rock vs. Rap” collection featured images of famous musicians or bands like Tupac Shakur, The Doors, Metallica, Pink Floyd, and The Notorious B.I.G.. After criticism from the public and several cease and desist letters from the estates of the musicians who were featured without permission, they pulled the shirts from their website and issued a joint apology. They met more heat in 2020 when reports of their clothing alleged factory workers in Bangladesh weren’t being paid due to the coronavirus pandemic.

Below are our favorite fashion looks by the icon herself:

  • Horseback Chic

    Kendall kicked off 2023 on horseback, wearing leather to keep her warm on the snowy mountainside. She kept her ears warm by wearing black fuzzy earmuffs and kept the blaring sun out of her eyes with some brown sunglasses. Kenny looks in her element, sporting a smile from ear to ear in the collage.

  • Sultry Kitten

    Using a cat emoji to accompany her femme fatale look is quite fitting. We see you, Kendall. Wearing a halter dress that is almost too see-through, the 5’11” supermodel lays on a bed and gazes into the camera.

  • Sunset Mirage

    She’s giving us inspiration for our summer closets. Here, Kendall wears a maxi dress with a gorgeous Renaissance print in vibrant sunset colors of orange and grey. She looks absolutely ethereal as she sits on an outdoor sofa, closing her eyes, letting the wind blow her hair away.

  • Vintage Vixen

    We are so jealous of the Kar-Jenners’ access to vintage designer pieces! Here, Kendall is wearing a gorgeous black and gold scalloped Jean Paul Gaultier gown at the Vanity Fair Oscar Party. In the clip she shares, you can tell she is enjoying herself, confidently posing on the carpet for photographers.

  • Parisian Beauty

    Before we even saw her croissant caption, Kendall’s look screams Paris. She knows how to be elegantly chic even when wearing all black. Wearing a scoop-neck black dress, rounded-point black shoes, and a thin black scarf wrapped around her head and neck, Kendall completes the stylish look with some black oval shades.

  • Textured and Structured

    For Milan Fashion Week, Kendall wore this gorgeous Bottega Veneta ensemble. Wearing dark shades of brown, Kendall sports a cropped mock neck sweater over a leather textured corset with a knee-length skirt featuring side slits. The whole look is so interesting, from the mixed mediums to the exaggerated structures of the skirt.

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