The Vintage Shoe Trend We'll See Everywhere In Winter 2025

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With its baggy jeans, love of dad sneakers, and obsession with all things minimal, Gen Z's motto seems to be that it's better to be underdressed than overdressed. But the tides are turning on the footwear front with an unexpected recycled trend set to hit just in time for winter: Grandma shoes are just one of the classic style trends staging comebacks in 2025. Whether it's a short block heel or a maximalist square toe, if you can imagine an elderly woman wearing it, it's fair game. 

"I think we're all looking for a change of pace from the sleek and minimalist styles of shoes we've been wearing over and over," notes Cynthia Kennedy, personal stylist, image consultant, and creator of Your Style Transformation Academy. "The old-fashioned shoes I would've never worn when I was younger are now one of my favorite go-tos! Those buckle, square-toed, low block-heeled and Mary Jane styles are being seen everywhere, and it's impossible not to see why." Speaking exclusively to Glam, Kennedy reveals that footwear like this creates "a lovely nostalgic feel" and is a particularly good match for "midi skirts, cardigans, tailored trousers," and other preppy-coded staples. "This ties into the 'old money aesthetic' trend with timeless quality pieces and preppy vibes — the total opposite of fast fashion. What's even better is they're comfy enough to wear all day," Kennedy explains.

When it comes to specific pieces for this shoe trend that everyone is trying in 2025, Kennedy recommends the WEANDWEI Women's Loafers. "Since these loafers have a chunky heel, I would balance them out with slim or structured pieces on top and bottom to avoid an all-over bulky look," she explains. "They're the perfect blend of classic polish and modern edge, giving you style and comfort."

There's no specific trick to incorporating your grandma shoes into the rest of your outfit as long as you strike a balance. "My favorite way to style these shoes is with something a little sharper or more tailored like a sleek coat to balance the sweetness," Cynthia Kennedy shares exclusively with Glam. "You can also try them with cropped trousers and a fitted turtleneck, or a midi-length wool skirt, tights, and a chunky knit. They're also amazing with a blazer and straight-leg jeans cuffed at the ankle ..." The stylist warns that if you don't team the bulky grandma shoes with sleeker garments, the whole thing could end up looking "frumpy." Basically, avoid winter dress trends that are totally outdated. We're evoking grandma, but we don't want to be mistaken for grandma!

For an especially elegant look, Kennedy points to the Quince Italian Leather Cap-Toe Ballet Flat. "These adorable flats can be styled with everything from jeans and a sweater, to a pencil skirt and a tucked-in blouse for a classic office outfit," she says. "The cap-toe detail adds a touch of sophistication that can elevate your everyday basics." If you're looking to create an especially winter-friendly outfit, Kennedy recommends the comfortable Jack Rogers Women's Maddy Pumps from Bloomingdale's, as they "look great with thick tights or opaque stockings and a midi-length wool skirt or tailored wide-leg trousers with a fitted sweater and chic coat." 

On the higher end, Kennedy vouches for the "fashion-forward" Dries Van Noten Velvet Asymmetrical Sandals. "I've worn them with a tailored wool coat, fitted cashmere turtleneck, and ankle-length trousers to showcase the shoes," she recalls. "I love playing with proportions and contrasting textures to keep the outfit chic, elevated, and interesting."