Grandma 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 sneakers and impossible-to-walk-in platforms, there’s something irresistible and exciting about returning to footwear that prioritizes comfort without sacrificing charm.
Far from being a nostalgic nod, this trend resurrects the kind of practical elegance that characterized generations past. These new “grandma shoes” combine polished materials and restrained proportions with a retro flair that works well with any type of jeans. From the neatest straight line to the baggiest baggy jeans, there’s just something about pairing a classic shoe style with contemporary pants that signals good taste. Grandma would be proud.
Ahead, the grandma shoe styles we’re shopping for fall and winter 2025.
Almond-toe ballet flats
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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.
Low block-heel pumps
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