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

These 3 Colors Will Define Menswear in 2025
How to wear three on-trend tones—and eight foolproof picks for spring fashion.

Look Your Best This Spring With Luca Faloni’s Versatile and Stylish Dress Shirts
Luca Faloni delivers Italian craftsmanship with timeless style. From sumptuous piqué to breathable linen, their shirts combine luxury, versatility & heritage.

Where to Cop the Best Menswear on ’The White Lotus’
The best styling—and the worst people—you’ll find on television right now.