41. Jimmy Fallon

Occupation: Comedian/Host, Late Night With Jimmy Fallon

It’s hard out there, sartorially speaking, for a late night host. He can’t alienate his viewers (all of America), but he’s still gotta be interesting and charming enough to hold our attention. David Letterman held things down for a few decades or so, and Conan and his hair are definitely attention getting, but Fallon’s perfectly tailored suits, surprisingly charismatic wit and shit-eating grin take the cake.