The humble boat shoe has been around for a long time. Sperry Top-Sider originated the style with their signature Top-Sider shoe in 1935 and in the decades since, the Massachusetts-based brand has manufactured them for everyone from the U.S. Navy to preppy and sporting gents of all ages. But just because the iconic design hasn't needed much improvement for the past eight decades doesn't mean it couldn't benefit from a reboot.

After all, in an era of menswear when the “old money” aesthetic is being rediscovered by young people and all things “Dad” are being reworked in modern ways, it was only a matter of time before the quintessential prep slip-on was reworked. In 2024, the silhouette has taken on a more rugged air—gone are the candy colors and white soles, replaced with rough-out leathers and suedes, while some are grounded with thick lug soles. The end result is a little tougher and less blue-blooded. But the revival was inevitable. “Every few years there's another wave,” Lisa Birnbach, the author of The Official Preppy Handbook, recently told the New York Times.

Beefed up and ready for adventure, these new boat shoes pair well with fatigue pants and relaxed, washed denim but, of course, still look at home with your favorite chinos and summer suits. And despite all the changes, what remains is what always drew men to the shoe—an easygoing attitude and sturdy, non-slip soles. Here are a handful that are ready for days on the water or simply strutting down the street.