When it comes to recent trends, fashion has been borrowing from its elders. Case in point: the grandpa shoes craze sweeping runways, social media, and the streets alike. Rooted in functionality, the look spans a range of comfortable, walking-friendly silhouettes, from classic loafers to preppy boat shoes, with an unmistakably Pops-approved sensibility. Sure, dressing like your grandfather may not have been on your 2025 bingo card (pun intended), but make no mistake—the trend is anything but stuffy.
Glamour’s ‘grandpa shoes’ trend edit
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What’s driving the sudden interest in these silhouettes? “Heels still have their place, but there’s a clear appetite for silhouettes that feel practical without sacrificing style,” says Marissa Galante Frank, fashion director at Bloomingdale’s. That shift was especially apparent on the runways, where grandpa shoes abounded. “Fall 2025 brought a renewed focus on shoes that feel refined, versatile, and quietly confident,” she says, and “designers leaned into menswear-inspired silhouettes that bring structure and polish, but styled them in a way that felt relaxed and modern.”
Oxfords—a silhouette defined by its closed-lacing system—were spotted at the likes of Calvin Klein and Bally. Derbies, known for their open-lacing look, had a moment at Victoria Beckham and Celine. Meanwhile, the boat shoe trend continued apace at Monse, which offered a cozy shearling-covered pair. And if the spring 2026 season was any indication, the footwear trend won’t be falling by the wayside anytime soon: Heavyweights like Loewe, Prada, and Jil Sander all took stabs at grandpa shoes.
Thoughtful styling is the key to making these classic silhouettes feel both chic and of-the-moment. For instance, juxtaposing grandpa-looking footwear with more dainty, ladylike looks is one way to breathe new life into the shoes, according to stylist Elizabeth Cardinal Tamkin: “I like contrasting them with unexpected pieces, like a lace slip or a big skirt—something feminine!” In her opinion, this type of mashup makes your outfit feel like an original creation, not a rehash of something your grandfather might actually have worn.
Still with us? Below, shop four grandpa- and editor-approved shoe styles we’re adding to our 2026 lineups.
The loafer
Neil Mockford
By Kelsey Stewart
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