During the 1960s, a generation gap emerged in styles of men's hats. Some formal hats continued to be worn by men of working age, while the headgear of the younger generation tended to be part of a larger fashion or political statement. Overall, however, the hat became less ubiquitous than it had been in the 1950s. (See Reference 1.)
The Peaked Cap
Made of suede, felt or corduroy, the fisherman's-style peaked cap was a throwback to the Beatnik movement of the 1950s, exemplified by Jack Kerouac's “On The Road.” It was typically worn with a suede or sheepskin jacket. It reached the height of its popularity in the mid-1960s. Pop stars such as John Lennon and Donovan wore them, but it will forever be most closely associated with Bob Dylan, who sported one on the cover of his debut album.
The Wide-brimmed Hat
The wide-brimmed hat came into its own during the psychedelic era. It could be worn with hip items such as mock-Regency tunics with raised collars, flowing silk shirts and fur coats. The wide-brimmed hats perhaps best-remembered today are those worn by Jimi Hendrix in concert, who enlivened the headband with feathers and Native American beads. Another great exponent was Sly Stone of Sly and the Family Stone.
Cuban revolutionary Che Guevara turned the humble beret into a style icon. As flower-power gave way to a more militant mood, the beret was adopted by would-be revolutionaries in many countries. In Britain, a combat jacket from the Army and Navy Surplus Store and a Che Guevara T-shirt would complete the look. In the U.S., it became particularly associated with the Black Panther movement, and it caused controversy when it was worn by some African-American athletes at the 1968 Olympic Games in Mexico.
In America, the fedora, with its pinched crown and drooping brim, continued to be popular with the average family man at least until the mid-1960s. Over the years the brim shrank in size, lessening its use as a practical protection from the elements.
The Bowler Hat
The “bowler” was noted for its hard crown and curled brim. It was still popular in business circles in Britain at the start of the decade. By the end of the 60s, it was rarely seen outside of the square mile of London's financial district.