Q: How many hats do you own?
A: Some would say that my hats are as numerous as the stars in the heavens and the sands on the shore. Others would put the number at about 16.
Q: What does a fedora say about a person that a baseball cap cannot?
A: It says “look at me, I’m both an adult, and I have a sense of style.” I will say, though, that a lot depends on what else is being worn. Depending on the rest of the fit, a baseball hat may be far more appropriate than a fedora.
Q: Do you exhibit favoritism towards certain hats?
A: Yes, but I don’t want to say which ones for fear of offending the others.
Q: Do you feel incomplete/ bald when you aren’t wearing a hat?
A: Alas, for the decade or so, I’ve felt somewhat bald even when I am wearing a hat.
Q: What is the first hat you remember buying?
A: I think it was a gray fedora that I bought at a thrift store in Nashville, but it would be about 39 years ago, so perhaps I can be forgiven for not remembering. It’s not like asking about my first pair of black and white wing-tip shoes.
Q: Where do you buy your hats?
A: I’ve bought them in thrift stores, hat stores, Poshmark, Ebay, amazon, and occasionally on the street.
Q: Do you ever hide anything under your hat?
A: Please see earlier comments re balding
Q: How do you decide what hat to wear when you wake up in the morning?
A: On a good day, I have chosen my ensemble the night before, but the real question is what else am I wearing. A hat turns an outfit into a look. There are times, however, where I particularly want to wear a certain hat, and will choose the outfit accordingly. .
Q: What is the strangest way you have acquired a hat?
A: I got a variety of hats for serving in the US Army. While I did not do so for the purpose of getting any of those hats, I do think that it probably counts as the strangest way I’ve acquired a hat.
Q: Are there hats you reserve for extra special occasions?
A: Some days are more feztive than others.
Q: At what point does owning many hats become a lifestyle rather than a hobby?
A: I find the term “many” to be problematic. I’m sure you see your twenty digits as “sufficient to your needs” rather than “many.” So in answer to your question, it becomes a lifestyle when you begin to feel that you need to justify to other people the amount of hats you own.
Most importantly…
Q: Is there a proper way to wear a hat?
A: Mr. Deutsch did not defeat the Soviet Union in the Cold War only to come home to a country where people have to wear their hats a certain way. This is America, and you can wear your hat any way you want to. But while you may choose to wear your hat as you see fit, yes, there is a proper way. To quote from Frank Sinatra and Dean Martin in Robin and the 7 Hoods, “A flower’s not a flower if it’s wilted, and a hat’s not a hat til it’s tilted.” Tilt if forward, backwards, any side you want, but a hat worn well should have a little rizz of its own.
