Chukkas

Why

It's a classic shoe that has seen a good amount of updating for 2015, thanks to fresh colorways and modern, athletic-inspired soles.

Origins

The "chukka" name is derived from the game of polo, as early models were akin to the boots worn by British polo players.

How to Wear It

Pair them with your beat-up jeans and worn-in cotton chinos. Let them give your suits and wool dress pants a shot of relaxed cool.

What to Look for

A comfortable fit, a flexible sole and a color that will complement your wardrobe.

Shown left: $179.15 / $119 by Timberland