Redford and Newman. Clooney and Pitt. Sinatra and the entire Rat Pack.
The bond between two incredibly stylish men is a special one—and, more importantly, makes for some especially handsome photo ops. But like all great romances, some were fleeting, others stood the test of time and at least one ended in litigation. So we’re taking a look back at the proud history of menswear style icons hanging out with one another.