Kendall Jenner Takes Some Business Wear Pointers From Hailey Bieber

Kendall Jenner at the Hennessy x Renell Medrano
s Ice Magazine Vol. 2 Launch held at WSA on September 13 2025 in New...
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Elevated business attire is a Hailey Bieber calling card—and it looks like her penchant for power suiting has rubbed off on her pal Kendall Jenner.

Jenner stepped out amid New York Fashion Week last night for a party celebrating the launch of photographer Renell Medrano’s Ice magazine’s second issue at the WSA. The model and recent Vogue cover star opted for an I-mean-business gray check midi dress with a v-neck and pencil fit skirt by Dolce Gabbana, which she styled with her favorite pair of deep red spectacles from Lexxola, a large black envelope clutch from The Row, and black pointed stilettos. She wore her hair pulled back in a serious slicked bun, for maximum ’90s boardroom presentation impact.

Mona Tougaard Kendall Jenner Renell Medrano and Justine Skye at the Hennessy x Renell Medrano
s Ice Magazine Vol. 2...
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NEW YORK NEW YORK  SEPTEMBER 13 Kendall Jenner seen in Financial District on September 13 2025 in New York City.
Photo: Getty Images

Joining Medrano, Kendall also posed with fellow model Mona Tougaard and Justine Skye.

Power suiting, sharp skirt suits, and tailored silhouettes are certainly going to be something we see more of for fall, whether that’s in the sleek and chic Hailey Bieber style or a more English heritage gone glam take by Demi Moore. On a recent trip to New York, Bieber celebrated her brand Rhode’s first retail expansion at Sephora with a suite of business wear-informed outfits, with some Hailey-esque twists of course. Bieber wore a dove gray archival Donna Karan set, a Calvin Klein pinstripe suit, and a buttery leather blazer from Tom Ford-era Saint Laurent with a black lace bra peeking out.

NEW YORK NEW YORK  MAY 05 Kendall Jenner attends the 2025 Met Gala Celebrating Superfine Tailoring Black Style at...
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Image may contain Kendall Jenner Clothing Formal Wear Suit Blazer Coat Jacket Helmet Adult Person and Footwear
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The Kendall Jenner compendium of style is accustomed to a corporate-leaning look too, though, with a wardrobe that includes relaxed suits via her beloved The Row. She also tapped independent British designer Torishéju Dumi—of the label Torishéju—for her impeccably tailored 2025 Met Gala look. A simple, sharp dress and exquisitely tailored situation is perfect for a model on-the-go, and with international fashion weeks and awards season amping up, expect to see more serious fits from Jenner on the streets.