world of men's style / fashion / grooming

An UrbanDaddy Publication

The Icon: Late-Night-Era Letterman

David Letterman

Talk show hosts aren’t usually the most sartorially advanced folks, but once upon a time, there was an exception. Allow us to roll back the clock 30 years or so, and introduce you to a young man named David Letterman…

Perfectly Embodied: Take it all in: the blazer, the hair, the tie clip. The immaculate 80s musk of it all. He’s just well-dressed enough to be courteous, but not so buttoned-up that he can’t have a little fun. Three Days of the Condor gets all the hip references, but for our money, Dave pulled the look off better and more often than Redford ever cared to. Of course, as he’s become more of an institution, he’s settled into cigars and double-breasted suits (not the Italian kind), but we still remember the puckish youth with the fierce loyalty to rough wool.

Words of Wisdom: I had no idea this thing was televised. Boy, is my face red.

The Backstory: It always helps to look like you’re having fun. That particular quote was meant to laugh off his first Oscar-hosting gig, but it applies pretty well to the man in general. When you make your living poking fun at brittle celebrity, looking the part is crucial—and he always has. As it turns out, you can get away with a whole lot more when you’re wearing a repp tie.