Bond has worn chukka boots in the last four films, from Die Another Day to Skyfall. The classic chukka boot is made in brown suede, and from English makers today they are most often found with Dainite® rubber studded soles. The standard chukka is a two-eyelet design, but they can just as often be found with three eyelets. Bond usually wears them in brown suede, and in Casino Royale and Skyfall he wears chukkas in calf as well. For the most part, Bond’s chukkas have Dainite® studded rubber soles, except the boots in Die Another Day have either soles of leather or a combination of leather and something else. Chukkas are casual boots, and Bond mostly wears them casually. Roger Moore wore them more formally with his country jackets in The Saint. Daniel Craig went even further with them in Skyfall, wearing them with his grey pick-and-pick suit. But balmoral boots, oxford boots or chelsea boots—like Sean Connery wore in Thunderball—are a better match for the formality of a suit.
In Skyfall, Daniel Craig also wore a variation on the chukka: the desert boot. The desert boot is a chukka—typically suede—with a crepe sole. As the name suggest, they are great to wear in sand. The ankle height prevents sand from getting inside the shoe whilst the crepe soles are very comfortable for walking on sand. Daniel Craig wears his on the beach, but he makes sure they stay dry. On the city pavement crepe soles absorb the dirt off the street and wear out quickly. Craig’s desert boots are light brown suede.
The chukka boot once again returned in Spectre, this time in the form of the Sanders & Sanders “Hi-Top” chukka boots, also known as the “Playboy” chukka boots. The boots are snuff suede with a two-eyelet closure, a full leather lining and crepe soles. Crepe soles are associated more with the desert boot, the chukka boot’s brother. Crepe soles are made of coagulated rubber and are very soft and comfortable and fantastic for the desert, but they’re not a good choice for the city. On pavement they absorb all of the filth, and in the rain they become very slippery. And as the soles age they harden, crack and lose their spongy comfort. The “Playboy” chukka boots are one of Daniel Craig’s Bond’s wardrobe items directly inspired by Steve McQueen.