Vittoria Ceretti Proves Checkered Vans Are the Key to Lazy-Cool Dressing in 2025

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Vittoria Ceretti may be Gen Z, but she wore her checkered Vans like a true millennial.

On September 26, the 27-year-old model was spotted in Milan wearing a casual travel look consisting of low-rise sweats layered over plaid boxers, which she paired with a plain black T-shirt, oversized shirt jacket, and the same pair of shoes every millennial scene kid purchased from Journey with their first mall paycheck.

Though checkered Vans instantly summon memories of ripped skinny jeans and flannel over-shirts, Vittoria Ceretti’s outfit combo could easily be plucked out of any high school homeroom in 2005. Of course, her Chanel purse, chic rectangular sunglasses, and general aura elevated the tone of the look for a model off-duty in 2025.

Vittoria Ceretti is seen in Milan on September 26, 2025.

Robino Salvatore

Ever since Timothée Chalamet brought out his Alexander McQueen skull scarf in January, I’ve been waiting for the return of checkered Vans, though other Glamour editors have been predicting their resurgence even longer. In March of last year, Glamour commerce editor Jake Henry Smith noted that celebs like Emily Ratajkowski and Morgan Stewart McGraw had been quietly adding the skater shoe back into their rotation, offering readers a chance to “get ahead of the curve.”

Since then, early-aughts and 2010s fashion staples have only become more and more prominent among the fashion set, whether it’s a deep pull like Chalamet’s skull scarf or more classic, understated pieces like ballet flats and skinny jeans, which can be incorporated into modern wardrobes without feeling referential. Checkered Vans fall somewhere in the middle, instantly evoking millennial nostalgia without requiring much effort to style.

Another solid way to style checkered Vans in 2025.

Edward Berthelot/Getty Images

No notes.

Daniel Zuchnik/Getty Images

In fact, the less effort the better, as the functionality of Vans are kind of the whole point. Of the many features engineered for skateboarders, their cushioned insoles—which absorb impact during a skater’s landing—make them one of the most comfortable options on the market, while the slip-on design of the throwback shoe make them ideal for airport security checks.

Whenever sweatpants are a wardrobe requirement, checkered Vans are a simple way to add a dose of personal style to your look. On the flip side, they can instantly relax a more polished ensemble for a more laid-back appearance. Frankly, I can’t think of a millennial statement piece more worthy of resurgence—even if you weren’t old enough to attend Warped Tour without adult supervision in 2008.

Vans Classic Slip-On Checkerboard Sneakers

Vans Classic Slip-On