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
For an easy entryway into the grandpa shoe trend, slip into loafers. (We’re almost certain you already have at least one pair in your closet.) A classic black style works just as well with your work trousers as a sheer midiskirt. However, if your 2026 resolution is to step outside the box with your style, consider dipping your toes into suede pairs or tassel-adorned picks—or, better yet, a style like Free People’s that boasts both.
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The oxford
Fun fact: In the early 1800s, oxfords became popular among Oxford University students, who were seeking comfier, low-cut alternatives to bulky footwear. Today, the lace-up silhouette is just as compelling. Yes, these are definitely something your dad (and grandpa, of course) has worn at one point. But thanks to brands like Scarosso and Camper, the newest oxfords on the market have a cool-girl edge ideal for styling with spring’s high-volume silhouettes.
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The derby
If you’ve been wearing the same rotation of sneakers and ballet flats ad nauseam, consider giving derbies a spin. Similar to the oxford but with a slightly looser closure that’s a little less formal, the silhouette is a key player in Celine’s buzzy spring 2026 collection. Although the label’s iteration is especially slim, other styles out there feature low heels or platform soles for those who prefer a bit of a lift.
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The boat shoe
With the preppy fashion revival in full force (hello, cable-knit sweaters and rugby shirts), boat shoes will be sticking around in the new year. While the silhouette is arguably most worn in the spring and summer, don’t rule them out during the chillier months—simply pair the shoes with cashmere socks for warmth. (The grippy soles, designed for slippery decks and docks, are also great for slushy streets.) If you’re worried about your boat shoes reading overly collegiate, offset the look with an edgy leather jacket and slouchy jeans.
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