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Kendall Jenner Won the Office Siren Trend This Weekend

The supermodel and entrepreneur was styled by Dani Michelle for the Hennessy x Renell Medrano Ice Magazine launch party.

Ananya Panchal

Kendall Jenner
Kendall Jenner / Theo Wargo/Getty Images

Kendall Jenner is no stranger to setting trends, and this weekend, she brought the office siren aesthetic to New York Fashion Week in the most elevated way possible.

The 29-year-old stepped out for the Hennessy x Renell Medrano Ice Magazine Vol. 2 launch on Sept. 13, held at WSA in NYC, and instantly turned heads with her striking corporate-meets-coquette look. She wore a vintage gray plaid midi dress, featuring a plunging V-neckline and tailored pencil silhouette, from Dior’s Spring 2004 collection.

The archival piece hugged her slim, sculpted frame and accentuated her famously tiny waist, giving her the sharp, clean lines of a ‘90s power dresser—without sacrificing any of her signature sleekness. The menswear-inspired print combined with its feminine cut made it an ideal candidate for the office siren trend, which continues to dominate runways and street style alike.

The supermodel leaned all the way into the corporate-chic theme with accessories that added a sophisticated twist. She completed the outfit with sharp black pointed-toe pumps from The Row. Her hair was styled in a tight, slicked-back bun for a no-nonsense, boardroom-ready finish.

Kendall Jenner
Kendall Jenner / Marsha Bernstein/Getty Images

To bring in just a touch of scholarly whimsy and personality, she added a pair of black rectangular eyeglasses from Lexxola—her current eyewear obsession and the statement piece that tied everything together. Tiny silver earrings peeked out subtly from beneath her pulled-back hair, proving that less really is more.

Styled by longtime fashion collaborator Dani Michelle, who sourced the archival look from Aralda Vintage, Jenner shared a carousel of moody, mysterious photos from the event on Instagram. Dim lighting, soft expressions and sharp styling set the tone—serving major sexy CEO energy.

The look is a fresh departure from the lacy dresses and see-through trends we’ve seen all season from Jenner—but just as unforgettable. With this appearance, she reminded us that power dressing can be sensual, and that vintage tailoring, when styled right, feels anything but dated.

“Obsessed!! Glass of red wine missing,” Scotty Cunha commented.

“Glasses add prestige. Lady with a capital L,” one fan gushed.

The 818 tequila founder’s glam was glowy and fresh as always, featuring her signature foxy eye makeup, berry blush and a fall-coded deep warm taupe lip.

Jenner, who recently appeared on the cover of Vogue alongside Gigi Hadid, opened up about her evolving priorities and vision for the future. “There is a lot of superficiality in the world that we work and live in,” she reflected. “And our personal lives have been of public interest as we’ve gotten older.”

Despite her deep roots in fashion and entertainment, she teased a potential shift in focus. “I swear to God, I’m going to stop everything and just design homes,” she said, revealing she’s currently building a house out West. “I love my space in L.A., but I also really love the simple life. I like getting up every morning and throwing on a bathing suit or sweatpants and no makeup and just being free with my day.”

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