Here’s a joke from 3rd grade: why do Indians wear feather headdresses? …… To keep their wig warm. One of the main reasons to wear a hat is to keep your head warm. Men generally wear hats outside only, and mainly to keep warm, or to keep the sun off your eyes. We thus show below a delivery boy in a knitted cap (called at torque in Canada), and a boss is a stylish fedora. The two hats keep the head warm, but the fedora protects the eyes too, and the different styles establish who you are in the social chain. It is a good thing when fashion works this way, and uncool, in my mind, when messages are reversed or unclear. It’s equally uncool to see a delivery boy in a fedora as an executive in a wool cap. Either one looks pretentious to me. One is dressing up, the other dressing down or confused. Women’s hats generally look confused to me, in part because there is no such thing as a real business-woman’s hat.

Nowadays, many business men don’t wear hats, even outdoors in the sun and cold. This seems like a bad idea, but what would I know? Perhaps the problem is what to do with the hat when you come indoors. You can take it off, but then what. Emily post claims that leaving the hat on indoors is usually considered rude, though not always, and traces this back to medieval knights and to the flag code. Indoors, the delivery boy can stuff his knit hat into his pocket, or roll it into a smaller version on his head, a beanie. The fedora wearer must look for a hat rack, or accept looking rude.

Of course the lack of a hat presents problems too. Without one, you leave your hair to signal your social status and political cultural associations. For a man without a hat there are only three styles of hair: short, medium, or long. Short hair says you are a conventionalist drone, long hair, that you’re a hippy or artist, and with middle-length hair you’re …. uncertain? trans? androgynous? No matter how you slice it, it’s not a good look. Adding a mustache or beard makes it even more awkward, in my opinion, see below. I have previously written about the power of mustaches — that they send a message that you are warrior, and beards — that you are a man of fervor, — or of religious or aristocratic sympathies. But combine a mustache with middle-length hair and you begin to look like another Hitler or Stalin.

Wearing a hat allows for a great variety of social messaging, whether worn with or without facial hair. Some hats are expensive, others cheap; some signal religious affiliation, others are strongly secular, or hip. Some folks wear hats that are suitable only for work or sports, like a hard-hat, bicycle helmet, or a straw boater. They tell folks you’re busy with an activity right now. But most people who wear hats, choose one that’s multidimensional, suitable for sport and work. There is the classic Kangol cap that suggests a certain artsy vibe, or the peak cap or newsboy — that suggests (I imagine) a higher level of worker.

Perhaps the most popular flex-hats in the US are the baseball hat, and its relative the trucker’s hat (you adjust the size on a truckers hat using a band int he back). In the US, you can wear these on the job, or off. I think they work indoors too, but what do I know. The baseball and peaked cap suggests you are higher on the social ladder than the truckers cap, but all of them suggest you draw a paycheck. And they often say a lot more. If your trucker’s hat says, NRA, or John Deere, or Oakland As, there enough information given to start a conversation. Depending on what your cap says, you will be welcome in some societies, not welcome in others. Don’t wear your MAGA hat to a Biden rally.

There is power in hats too. A man in a policeman’s cap is a cop, even if he’s without the rest of his police gear. With no hat, the same man in uniform is a mall security guard. The postal person or UPS delivery person is on the job if wearing his USPS baseball cap or knit. An expensive visor cap, like the kangol suggest artistic status, and an expensive newsboy, or peaked cap. suggests a sort of work-life balance. It was worn by Prince Charles in the 1980s, and by me in 2020.

Although a fedora is a boss-man’s hat, I never wear one since I associate them with mobsters, hipsters, lounge singers, and Jimmy Hoffa. For more formal occasions, when not wearing a peaked cap, I wear a Homburg. Churchill wore a Homburg. In England, there is a level above this, the top-hat, and one slightly between the Homberg and fedora, the derby. In the US, none of these really caught on. The derby is sort of comic, sort of social climber. Chaplin wore one, as did Laurel and Hardy. Derby hats tend to get punched through in old-time comedies. It’s the same with most middle of the road approaches — they appeal to no one.

Robert Buxbaum, March 5, 2020.