Kendall Jenner Masters ’90s Boardroom Glam at Ice Magazine Launch • CelebMafia

Kendall Jenner just redefined power dressing—swapping the expected for a sleek, houndstooth sheath and a dash of intellectual flair (those red frames!) at Renell Medrano’s Ice Magazine soirée.

There’s something deliciously subversive about Kendall Jenner’s latest sartorial move. Amid the whirlwind of New York Fashion Week, where bold prints and avant-garde silhouettes often steal the spotlight, Jenner opted for a look that whispers rather than shouts—yet commands attention all the same.

Jenner’s choice—a sleeveless, houndstooth midi dress—is a masterclass in understated sophistication. The fabric, a structured wool blend, clings just enough to hint at the body beneath while maintaining an air of professionalism. The deep V-neck adds a touch of allure, but the real star is the pencil skirt, its sharp lines and knee-grazing length channeling the polished authority of a ’90s power broker. It’s a silhouette that feels both nostalgic and refreshingly modern, a nod to the era’s minimalism but tailored for today’s red carpets—or in this case, the cobblestone streets of NYC

The accessories are where Jenner’s signature flair shines. Her oversized red-framed glasses (a Lexxola favorite, if we had to guess) inject a pop of color and a scholarly edge, transforming the look from corporate to creative in an instant. In her hand, a black envelope clutch—likely The Row—sits like an extension of her arm, its sleek lines mirroring the dress’s precision. And those shoes: classic black stilettos, pointed and polished, the kind that promise to carry you from a board meeting to a midnight soirée without missing a beat.

Jenner’s look arrives at a moment when power dressing is experiencing a renaissance. From Hailey Bieber’s sleek suiting to Demi Moore’s glamorous takes on English heritage tailoring, the fashion set is embracing structured silhouettes with renewed vigor. Jenner’s houndstooth dress, with its nods to ’90s minimalism and boardroom chic, feels like a natural evolution of this trend—one that swaps the expected blazer for a dress that’s equally commanding.

There’s also something delightfully meta about the choice. Houndstooth, after all, is a pattern with a storied history, evoking everything from mid-century modernity to punk rebellion. Here, it’s reimagined for a new generation, its graphic lines softened by the dress’s fluid fit and Jenner’s effortless cool.

The magic of this look lies in its cohesion. The sleek bun, the minimal makeup, the bold glasses—they all serve to highlight the dress without competing with it. Even the wineglass, held aloft in the second image, feels like a deliberate styling choice, a reminder that power dressing isn’t just for the office. It’s for the after-parties, the impromptu toasts, the moments when confidence is your best accessory.

For more inspiration on how the fashion elite are redefining celebrity style, look no further.

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