There are certain materials and terms that are common in shoe descriptions—rubber sole, suede exterior, NBA star names—but every once in a while you stumble upon one you don’t see too often. In the case of the Sperry Top-Sider 7-Eye Boot, you stumble upon far more than that. Uppers with wool flannel trim, rust-proof eyelets, a shock absorbing heel and other manly features you won’t find in those fancy sneaks your lady just bought you for “clubbin” are jammed into this pair of Sperry’s. Listen, you know any pair of shoes originally designed in the 1930’s aren’t meant for guys who get mani-pedis. These are boots from the time when a guy came home from a long day with dirt on his face regardless of occupation and they just happen to look stylish as well.
More Fashion
The Coolest Father’s Day Gifts of 2026 (New Products Added 5/19)
A curated collection of the best Father’s Day gifts for dads who appreciate craftsmanship, clever design, great stories, and really cool stuff.
An Ode To Kapital, One of the Coolest Brands in Japanese Menswear
On a recent visit to Tokyo, I fell in love with the cult-favorite label.
The $95 Sneakers Your Fashion Friends Will Ask You About
The retro-inspired runners that got us out of a style rut.