Spier & Mackay Unlined Suede Chukkas – $228 About the Author: Adam Terry is a thirtysomething sales manager in the construction industry. He enjoys fine watches, boots/shoes, raw denim, and working on his dad bod father figure. Few shoes occupy as elegant a middle ground in menswear as the chukka boot. Where its cousin the desert boot leans casual with a crepe sole and relaxed silhouette, the chukka’s taller shaft and harder sole push it into genuinely versatile territory.