world of men's style / fashion / grooming

An UrbanDaddy Publication

Style Icons on Dates

  • Najib Benouar

Steve McQueen

Valentine’s Day isn’t till tomorrow, but you can already feel it in the air: the unmistakable tingling of a bone-chilling winter frost.

But also: romance.

And since you’re more than likely on the hook for dinner, or at least a starry-eyed stroll, we thought you could use some inspiration for tomorrow’s festivities—with some style cues from history’s most fashionable gents on dates. Just don’t forget the flowers (or in the case of Mick Jagger: cotton candy).

Without further ado: 10 ridiculously good-looking dates and the style icons who love them.

Style IconsSean Connery and then wife Diane Cilento, 1960s

Style IconsRyan Gosling and Eva Mendes, 2011

Style IconsJack Nicholson and Anjelica Huston, 1970s

Style IconsFrank Sinatra and Mia Farrow, 1965

Style IconsWarren Beatty and Natalie Wood, 1962

Style IconsClark Gable and Carole Lombard, 1940

Style IconsBob Dylan and Joan Baez, 1963

Style IconsMick Jagger and Marianne Faithfull, 1960s

Style IconsMichael Caine and Natalie Wood, 1966

Style IconsSerge Gainsbourg and Jane Birkin, 1970s