Let's Settle The Great Fashion Debate Of Fall 2026: Are Sperry Boat Shoes Out Or On-Trend?

It's no secret that many of the beloved fashions of yesteryear are enjoying a modern-day renaissance, from lace camis to bootcut jeans, but can we count Sperry boat shoes among the resurrected? We've seen celebs like Jennifer Lawrence and Meghan Markle kicking around in soft leather tie-up shoes lately, and so Glam tapped Los Angeles-based personal stylist Charline Zeroual for her thoughts on whether the preppy boat shoes are back in for fall 2026. Of course, Sperry is the specific brand popular for that particular style of boat shoe, much like how Birkenstocks have become synonymous with casual double-strapped slide sandals. So, actual label aside, Zeroual says she does indeed expect Sperry-style boat shoes to be among the fall 2026 shoe trends everyone will be walking around in. 

Zeroual — who approaches her work with sustainability in mind as founder of the Sustainable Wardrobe Stylist — explains that boat shoes have quietly started to gain popularity over the last year or so, and she thinks that slow trickle will continue and that they'll soon become a go-to again. "They fit perfectly into the leather flat movement we're seeing right now, and into that urban preppy, East Coast-inspired aesthetic that feels very relevant," she explains to Glam exclusively. 

Zeroual notes that other millennial footwear staples are making a comeback and delivering all the nostalgic feels, and boat shoes are a practical and versatile option. "A ballet flat feels more feminine and delicate, a loafer more classic and slightly masculine, while the boat shoe sits somewhere in between. It has sporty attitude but still feels much more polished than a sneaker. I think balance is what makes it interesting again." Another pro for boat shoes? Because they're cute, casual, and comfy, count them among the fall 2026 fashion trends older women will love. 

To get in on the boat shoe trend in a fresh way and without looking like you're cosplaying as a Y2K-era private schooler, personal stylist Charline Zeroual says it's all in the styling. The key is to push against the shoes' preppy nature, so put that striped polo shirt down. "Bring some edge and don't fall into the full preppy look," she tells Glam exclusively. "Instead of the straight or tapered jeans we would have worn with them in the early 2010s, I would pair them with a longer, wider-leg jean or trouser. Add a beautiful relaxed cashmere sweater tucked in at the waist, or an oversized button-down worn slightly undone and half-tucked." Consider reaching for a pair of boat shoes instead of, say, sneakers if you're wondering how to make boyfriend jeans look sophisticated, not sloppy.

Also, it can be tempting to go no socks or opt for the obvious "funky" move of white sweat socks when slipping on boat shoes, but Zeroual says, "Try something unexpected: a statement color, texture, or even a subtle sparkle. Socks are becoming an accessory in their own right, and that small detail can completely change the attitude of a classic shoe." She explains that it's all about contrast and unexpected pairings. "Take something classic and push it in a slightly different direction. For me, that's what makes an outfit interesting: classic, but with an edge."

Ready to add a pair — or two or three — of boat shoes to your fall 2026 wardrobe? Glam asked personal stylist Charline Zeroual for a few of her expert, exclusive recommendations. She said, "Whichever version you choose, I would keep the rest of the outfit modern and a little unexpected. That is what takes the boat shoe from nostalgic to relevant." With that, let's browse.

"As a French stylist, I naturally love the Sacha Loafers from Sézane. The suede and shape give you that boat shoe feeling, but with a slightly more refined, Parisian point of view." Zeroual's first recommendation focuses on a brand from across the Atlantic, but she has spotlighted a U.S. option too. "My East Coast friends would probably tell you to go straight to the Eastland Seastar Boat Shoe. They have that authentic American boat shoe heritage, so if you want the classic version you really can't go wrong there." 

Finally, the expert can't leave a more environmentally friendly option behind. "As a sustainable stylist, I've also been recommending the Bared Footwear Tringa flat. I particularly love their suede versions. Some of my clients have tried the pink pair, and they loved them. It's a fun way to wear the trend without choosing the most predictable brown boat shoe."