The brown suede shoes that Sean Connery wears with his hacking jacket and cavalry twill trousers in Goldfinger and Thunderball are something people often ask me about. Thy are two-eyelet derby shoes in what essentially looks like a short chukka. The soles are dark brown rubber. The suede uppers, rubber soles and thicker laces make these more casual—but also more versatile—shoes. They work well with informal country wear like in Bond’s case, but they could just as easily be at home with a pair of jeans. They have a slight edge of formality over chukka boots, which allows them to be dressed up a little more whilst at the same time they can still be relatively casual shoes.
Daniel Craig wears very similar shoes with his grey linen suit in Casino Royale.