I went for the iconic 1950s look Sunday by combining three '50s items that more or less were only popular during the 1950s.
-Early '50s "Bailey of Hollywood" fedora with a pugree and brim stitching (interestingly, Bailey is still around though, like most mainstream hat companies today, their quality has suffered since the 1950s).
-Mid-'50s Pleated tie (pleated ties became popular in the late 1940s and died off before the 1960s as ties became too narrow to hold the pleats).
-1950s 'Ricky' jacket made of long-hair wool.
click to enlargeThis fedora is fairly rare and has that casual Hollywood/western look about it.