When it comes to the freshest trends, fashion is now drawing inspiration from the older generation’s wardrobe. A perfect example is the “grandpa shoe” craze, taking over runways, social media, and city streets alike. Rooted in practicality, this trend showcases a lineup of comfy, walk-friendly styles—from classic loafers to preppy boat shoes—all carrying that unmistakable, “grandpa-approved” charm. Dressing like your grandpa might not have been on your 2026 bingo card, but trust us, this trend is anything but dusty or dull. Here’s the proof!
What’s Driving the Sudden Buzz Around These Silhouettes?
“High heels still have their place, but there’s a clear demand for shapes that are practical without sacrificing style,” says Marissa Galante Frank, Bloomingdale’s fashion director.
This shift was especially visible on the runways, where grandpa shoes were everywhere. “The Fall 2025 season spotlighted shoes that are refined, versatile, and quietly confident,” she adds, noting that “designers turned to menswear-inspired silhouettes that offer structure and elegance, styled in a relaxed, modern way.”
Oxford shoes, known for their closed lacing, appeared at brands like Calvin Klein and Bally. Derby shoes, with their open lacing, were highlighted in Victoria Beckham and Celine shows. Meanwhile, the boat shoe trend sailed on, with Monse unveiling a soft, shearling-lined version. One thing’s clear: this footwear trend isn’t going anywhere soon. Fashion houses like Loewe, Prada, and Jil Sander have all reimagined grandpa shoes.
Thoughtful styling is key to making these classic shapes feel both chic and modern. Stylist Elizabeth Cardinal Tamkin suggests pairing “grandpa” shoes with softer, more feminine pieces:
I love mixing them with unexpected items, like a lace silk dress or a full skirt—something truly feminine!
She believes this kind of mix creates the vibe of a unique outfit, not just a recycled grandpa’s closet.
Still with us? Here are four grandpa-approved shoe styles that made it onto our 2026 list.
The Loafer
If you’re looking for an easy entry into the grandpa shoe trend, slip into a pair of loafers. Chances are you already have at least one pair tucked away. A classic black pair works just as well with tailored pants as with a sheer midi skirt. But if your 2026 goal is to step out of your style comfort zone, try suede versions, fringed details, or even a combo of both.
The Oxford
Originating in the early 1800s among Oxford University students seeking a more comfortable, low-cut alternative to heavy boots, Oxford shoes remain just as appealing today. Yes, this is the shoe your dad (and grandpa) definitely wore. Thanks to brands like Scarosso and Camper, the latest models come with a cool, “cool girl” edge, perfectly matching spring’s bold, voluminous silhouettes.
The Derby
If you’re tired of the endless sneaker-ballet flat cycle, give derby shoes a chance. Similar to Oxfords but with a looser lacing, they’re less formal and play a key role in Celine’s 2026 spring collection. While the brand’s version is sleek, other models come with low heels or platforms for those craving a little extra height.
The Boat Shoe
With preppy fashion making a full comeback (hello, knit sweaters and rugby shirts), boat shoes are here to stay this year. Though usually worn in spring and summer, you don’t have to give them up in cooler months—just pair them with cashmere socks for warmth. (The slip-resistant sole, originally designed for wet decks, also comes in handy on slushy streets.) Worried your boat shoes might look too collegiate? Balance them with a cool leather jacket and relaxed jeans.
