It wasn't Connery's sense of style that landed him the role of James Bond, nor for that matter his acting ability. It was the educated eye of producer Cubby Broccoli's wife, Dana.
"He moves like a panther," she told her husband, and a previously unconvinced Ian Fleming. Ultimately, as we know, Connery's blend of charm and cruelty earned him six outings as 007 and eventually made him one of Hollywood's most bankable leading men. That and the fact that perhaps only Cary Grant has ever looked so good in a suit.
Bond made Connery synonymous with bespoke British tailoring, then. But he was adept at an off-duty look, too. The man even managed to look cool in his trunks.