Hats used to be as common as shoes in America. You wouldn’t dare leave the house without one. If you were a gentleman, you wouldn’t dream of keeping it on indoors.
Now things are a little different. The guys who attempt to wear those kinds of hats — trilbies, fedoras, and panama-style hats, but also flatcaps — are either mocked mercilessly, or should be.
Fedoras and the like are not fun accents to add to your outfit. They are formalwear, meant to be worn with suits. They just don’t work in other contexts.
There are, however, two exceptions to this strict no-hat rule: If you’re one of the two people who can get away with wearing a wild hat. They are: a man who could have been alive when men did wear hats every day, back in the early 20th century; or Johnny Depp and quirky people like him (and even he is pushing it). If the hat in question is a baseball cap. While a bit sporty of a look, a baseball cap can be worn in more casual styles with a high degree of success.
Former President Barack Obama once said: “Here’s the general rule: You don’t put stuff on your head if you’re president. That’s politics 101. You never look good wearing something on your head.”
But now that Obama is a normal citizen, he’s subject to the same rules as the rest of us. And he seems to be taking advantage of that while vacationing on Richard Branson’s private island, wearing a baseball cap backwards on the way to the beach with wife Michelle. It’s essentially the perfect time to wear a hat.
Unless you’re at the beach or in a very casual setting, hats come off as strange and try-hard. There are so many easier ways to add interest to your outfit. There’s no reason to bring headwear into this. Almost every outfit that was paired with a hat would be better without that addition. (Business Insider.com)