It goes without saying that Hollywood is a great honer of style, producing well-dressed leading men that much of the world would like to emulate. Which movies are the best showcases of masculine cool? Ah, so many to choose from! Here’s part 1 of our list—all highly watchable and highly stylish.
The Talented Mr. Ripley
Rarely has a psychotic madman acted so charmingly or dressed so well as Matt Damon’s title character. Great supporting performances by Gwyneth Paltrow, Jude Law, Cate Blanchett and Philip Seymour Hoffman help to make this imposter’s tale massively entertaining. By turns languid and tautly suspenseful, the movie is a visual feast of 1950’s Italian and American style.
Frank Sinatra is the wisecracking Joey Evans, a second-rate singer who’s always working an angle. Torn between wealthy socialite Vera, played by Rita Hayworth, and callow chorus girl Linda, played by Kim Novak, he ultimately gives in to love and ends up with Linda. The style flows as much from Sinatra’s wisecracking as the way he inhabits his suits. And there’s that great Rogers & Hart score, featuring, among other standards, “Bewitched, Bothered and Bewildered.”
In his first performance as Agent 007, Daniel Craig wiped away the decades of kitsch and silliness that had adhered to the James Bond movie franchise. His Bond is caustic, gritty, violent and cynical, but he also cleans up well. Bond plies his romance with Vesper Lynd, played by green-eyed Eva Green, with not only wit but also intensity. Decked out in formalwear, they make one of the handsomest couples ever to grace the big screen.
The Thomas Crown Affair
Steve McQueen stars opposite Faye Dunaway in this elegant game of cat and mouse, in which wealthy thief Thomas Crown falls for insurance investigator Vicki Anderson, who is out to pin a bank heist on him. The bespoke clothing in this movie is great, as are the cars—notably the Ferrari 275 GTB/4 NART Spyder, the first of only 10 ever built, which Dunaway’s character refers to as “one of those red Italian things.”