The Boat Shoe
Is Back

Adam Bartoshesky (@captainbarto) wears some Sperrys in their natural habitat.

Sperry Top-Sider originated their signature boat shoe in 1935 and in the decades since, the Massachusetts-based brand has manufactured them for everyone from the US 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 all things "Dad" are being reworked, it was only a matter of time before the quintessential dad shoe was reworked for 2019. Prada kicked things off with a luxe, graphic take that made even the most diehard sneakerheads take notice. Other brands followed suit, with slicker and more modern interpretations of the classic slip-ons. What remains is what always drew men to the shoe—an easygoing attitude and sturdy, non-slip soles. Herewith, the ten best pairs that are anything but old fashioned.

Sperry's Top-Sider box


When the Sperry's Top-Sider debuted in 1935,
they sold for $4.50 a pair.