Granny shoes making a comeback in the trend cycle feels like a delicious irony. What once evoked bingo afternoons and hard candies has now become an object of desire for those who want that classic, quiet-luxury vibe.
In winter 2025, shoes typically associated with our beloved grannies—think square-toe silhouettes, short block heels, and discreet buckles—have resurfaced as an elegant footwear alternative. In a world saturated with casual trainers and impossible-to-walk-in platforms, there’s something irresistible and exciting about returning to footwear that prioritises comfort without sacrificing charm.
Far from being a nostalgic nod, this trend resurrects the kind of practical elegance that characterised generations past. These new “granny shoes” combine polished materials and restrained proportions with a retro flair that works well with any type of jeans. From the neatest straight leg to the baggiest baggy jeans, there’s just something about pairing a classic shoe style with contemporary trousers that signals good taste. Grandma would be proud.
Ahead, the granny shoe styles we’re shopping for autumn and winter 2025.
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Le Monde Beryl Regency Snake-Effect Leather Ballet Flats
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Almond-toe ballet flats
This slim, slightly pointed-toe flat is the very definition of effortless elegance, as Kendall Jenner proves above. Its minimalist silhouette fits naturally under straight-leg jeans to create a clean line that elongates the figure. The contrast between the stiffness of the denim and the softness of the leather shoe makes for a beautiful visual harmony, too. This look doesn’t seek attention, but it gets it through its refined simplicity. Ideal for fast-paced days at the office, this combo works best with button-down shirts, double-breasted blazers and other pieces that walk the line between casual and polished.
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Low block-heel pumps
With its minimal heel, closed-toe design, and high vamp, these sensible pumps feel like the perfect bridge between nostalgic and contemporary. With straight or wide-leg jeans, the style brings a warm and polished note that softens the denim, à la Dakota Johnson. These are versatile enough to pair perfectly with everything from a suede jacket to a chunky knit sweater for the kind of effortless elegance that’ll turn you into a street style star.
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Heeled loafers
Heeled loafers, as seen on the runway at MM6 Maison Margiela during the Milan spring/summer 2026 Fashion Week, are a grandma shoe with a lot of versatility. The practical block heel makes it ideal for barrel jeans as a way to balance all that volume, or go with cigarette jeans if you want an elongated silhouette. It’s the kind of shoe that doesn’t require much styling to shine.
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Classic Mary Janes
With its simple strap and subtle buckle, the classic Mary Jane shoe is back in a big way. Wear it with socks, baggy jeans and a fitted top for a modern outfit. As you can see from this street style look, the contrast between the wide silhouette of the pants and the delicate shoe is an unexpected, almost playful visual. It’s the kind of look that feels studied, not stiff, and is ideal for those who love to mix the romanticism of the ’50s with the irreverence of today.
Granny shoes represent a new balance between the everyday and the refined. Their charm lies not in following the latest fashion, but rather in embracing the timeless pieces that give even the most casual of jeans a sense of coherence and stylish sophistication.
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