Which icon let hats go out of style in 1960s?

Answer 1

There are a number of reasons why hats began to go out of style in the 1960's as a staple of menswear. Although John F. Kennedy did continue the tradition of wearing a top hat to his Presidential inauguration, he did not wear it as he was sworn in as President as had others had in the past.

An interesting fact about Mr. Kennedy is that he hated wearing hats, in general. There's a particular episode of Mad Men(in the first season) in which the advertisers at Sterling-Cooper assess Kennedy's appeal to voters in 1960, and Mr. Cooper complains that the man doesn't even wear a hat, so how could he possibly win the vote among older people? Cooper considers this an extremely sloppy thing to do. The younger Peter Campbell then brilliantly quips that Elvis (another youth with excellent hair) never wore wear hats, either, yet his appeal to the masses is never in question. It seems that the act of never wearing a hat gave a more youthful air to both Elvis and John F. Kennedy's style (who to this day is still the youngest elected President), and, both being extraordinarily handsome men who later became icons, defined a new era of men's style in the 1960's.

However, the real reason for Kennedy's reluctance to participate in what was then a staple dress code was because JFK was very proud of his hair, and he felt wearing a hat stifled a signature look of his. Photos of him (or really, of any of his brothers) wearing hats are pretty rare.