1. Samuel Beckett
Foxrock, County Dun Laoghaire-Rathdown
Like a fine whiskey (up to a certain point), Samuel Beckett's style got better with age. Best known as a bleek, tragicomic playwright, the Irishman was also successful at producing novels, poetry, and directing theatre. He may have won a Nobel Price in literature, but now he's also lauded for being stylish as hell. Seriously, if we look as cool as Beckett when we're this old and whithered, then we can die happy.