Amid all the ’90s fashion nostalgia, one trend has taken over the style scene: the midi pencil skirt.
Much of the renewed interest can be traced back to Carolyn Bessette-Kennedy. Recently embraced by Gen Z as a major fashion inspiration, her signature 1990s “quiet luxury” aesthetic has resurfaced as a timeless alternative to fast-fashion trends. The renewed fascination has also been fueled by the upcoming TV series Love Story, which explores her life with John F. Kennedy Jr..
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Carolyn Bessette-Kennedy Takes Over The 2026 Fashion Scene
Gen Z has been gravitating toward Bessette-Kennedy’s minimalist wardrobe—think headbands, flared black trousers, and sleek slip dresses—as the ultimate “old-money” style inspiration. But one piece in particular is seeing a major comeback: the pencil skirt.
One of her most memorable looks featuring the silhouette was photographed in November 1996, shortly after her wedding to Kennedy. Bessette-Kennedy wore a beige pencil skirt from Prada’s Fall/Winter 1996 collection, pairing it with a simple black cashmere top. She completed the understated look with tall brown patent leather boots—also by Prada—creating an outfit that remains a blueprint for effortless, polished style nearly three decades later.
Kaia Gerber
In April 2024, Kaia Gerber offered her own take on spring fashion with an outfit reminiscent of Carolyn Bessette-Kennedy’s signature style—this time in sleek gray tones. The model wore a light gray, boat-neck, long-sleeve cropped shirt paired with a midi-length dark gray pencil skirt with a back slit. Gerber finished the look with silver satin kitten heels and a gold Cartier Panthère watch.
Kendall Jenner
Another celebrity embracing minimalist dressing right now is Kendall Jenner. Jenner has carved out a style identity that stands apart from some of her sisters, who often gravitate toward bold latex dresses and body-hugging bodysuits.
The supermodel was recently spotted during Milan Fashion Week wearing an effortlessly polished off-duty look. She paired a long wool pencil skirt with a black turtleneck layered over a crisp white shirt. Jenner finished the outfit with slim sunglasses and a leather shoulder bag, leaning fully into understated elegance.
The tequila mogul has openly expressed admiration for the minimalist style of Carolyn Bessette-Kennedy. In a recent interview with Burberry for one of its campaigns, she named several of her fashion inspirations, including Jane Birkin, Bessette-Kennedy, and Mary-Kate Olsen and Ashley Olsen. The 30-year-old is frequently spotted wearing pieces from the Olsens’ luxury label, The Row, which reflects a similar minimalist aesthetic.
Hailey Bieber
Of course, no trend roundup is complete without Hailey Bieber showing her effortlessly cool take on it. In her recent Japan photo dump celebrating husband Justin Bieber’s birthday, the mom of one shared mirror selfies highlighting her outfits, including her modern spin on the pencil skirt.
The Rhode founder gave the classic piece a Matrix-inspired edge by styling a leather knee-length pencil skirt with a matching blazer, a gray sweater, and black leather boots. Known as the ultimate clean-girl minimal aesthetic icon, Hailey proves she can rock this trend in a timeless way while keeping it modern.
