
Eddy Merckx always wore his with an extra dash of style. Sean Kelly pioneered the poofy-top hat look with maximum "luft." That extra air was supposed to insulate and warm the rider's head — but let's be honest: it was just to look extra-boss.

In the '80s, bike messengers embraced caps and they leaked into street and popular culture, even hi-fashion. Caps became the most iconic cycling accessory. And it became permissible, even dare we say fashionable, to wear them off-the-bike.