Writer and photographer James Joiner is a senior correspondent for The Daily Beast.

Trendsetter

’Round midnight or just about any other time of day, the groundbreaking trumpet player dressed like the whole world was watching, and if they weren’t, they missed a class act.

CLASSIC

John Kennedy’s casual-but-classy cool look, the very embodiment of what was once widely known as ‘Ivy League’ style, is as hot as ever. But then classics never go out of fashion.