About Vintage Style Men's Hats

By Timothy Sexton

  • Overview

    Before the mid-1960s almost no man would venture out in public without wearing a hat. Watch any movie made before 1960 about contemporary America and you will be hard-pressed to find a male character without a hat. It is said that hats began to go out of style when President John F. Kennedy appeared at his inauguration topless. Too bad, because the hats that men used to wear before that decade ran the gamut of style and made the chapeau of today--the baseball cap--look positively dull.
  • Fedora

    The vintage style hat most likely to be worn by a male in America between the 1910s and the 1960s was the fedora. The fedora is that soft felt hat with the wide brim that is most often seen today during Halloween when people dress up as a gangster or Indiana Jones. The hat is usually worn pinched in at the sides and creased in the middle. It can be worn either pulled down low over the forehead or pushed back higher on the forehead, but with the brim pulled down over the eyes for a more worldly appearance.
  • Boater

    The boater goes by many other names, such as skimmer, sennit and basher, but they all mean the same thing: a round straw hat with a flat brim and cap. Boaters used to be quite popular among the yachting set, as well as among Southern lawyers in old Hollywood movies. Today the most likely place to see these once popular hats is atop the members of a barbershop quartet.


  • Bowler

    Ever seen that Rene Magritte painting of the guy with the apple obstructing the view of his face? That guy is wearing a bowler, which is a hard felt hat notable for its high, rounded cap. The bowler is probably best viewed as a more casual kind of top hat. A top-quality bowler should be strong enough to withstand much abuse before the cap can be damaged or even permanently dented. The bowler reached its peak of popularity toward the end of the 1800s, but remains a favorite vintage hat among those seeking to add a little style and differentiation to their appearance.
    Big Bill Haywood wearing a bowler.
  • Newsboy Cap

    Also known more elegantly as a Gatsby, this cap was a favorite among those who drove the classic roadsters of the Roaring Twenties, as well as the newsies who withstood the harsh winter winds to make sure people could read newspapers. The cap looks like a regular cap with a hard brim, but over the top is lain a softer and fuller cap that may or may not be attached to the hard brim with a snap.
  • Pork Pie Hat

    An iconic and quintessential element of the rude-boy subculture of Jamaica, as well as among aficionados of ska music, the pork pie hat is often confused with a fedora. Essentially, a pork pie hat is a fedora with a hard cap, a smaller brim, and is worn without the same pinch and indentation that gives the fedora its unique styling. The pork pie has been the style of choice for people as diverse in personality as Dean Martin and Robert Oppenheimer.
  • Panama Hat

    Panama hats are quite popular in tropical climates because their light color reflects the rays of the sun away from the head and they are incredibly lightweight hats to wear during the sultry days of summer. An authentic Panama hat is woven from the leaves of the toquilla straw plant of Ecuador and features a rather soft and floppy brim. The popularity of the Panama extends to three Doctor Who incarnations and the fact that the hat remains quite popular in those tropic cultures long after many other hats became little more than a conversation piece.
    Harry Truman's Panama hat.
  • Tyrolean Hat

    Generally associated with either Robin Hood or Bavarian dancers at Oktoberfest, the Tyrolean actually experienced two separate periods of great popularity separated by half a century. The typically green soft velour hat with the very small brim and the dramatically shaped cap first became renowned during the 1880s before falling out of favor. When Errol Flynn wore a Tyrolean in the 1938 film "The Adventures of Robin Hood," he ushered the hat back into style for another decade. Today the Tyrolean hat is most often seen outside of the Alps in Oktoberfest celebrations.
    Tyrolean hat.
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