Michael Caine was the Windsor knot that tied the look of Swinging London together. The British actor famous for his Cockney delivery (“ED-U-CATE-TING REE-TAH”), big-frame glasses (both shades and prescription), trench coats over three-piece suits (turtleneck or Windsor)—and most importantly, leading roles in classic films such as Alfie (1966), The Italian Job (1969), and Get Carter (1971)—was panache personified.

It was a look as on-point as the Sterlings and Colts he put to use in his breakout role as a military spy in 1965’s The Ipcress File—casually killer, effortlessly “live a little,” the James Bond we never had. Caine was a cool, cucumber-garnished Tom Collins seeking vengeance—or a lady friend—in the shipyards and tenements of South London.