Thoughts on Hats

  • First of all, people don’t wear them enough. People who habitually wear hats, even when the weather doesn’t demand it, tend to be cooler than people who don’t. We all know this, so don’t even try to argue.
  • There’s a theory that President Kennedy killed the hat industry. JFK was born into a generation that did not venture outdoors without some kind of hat. Be he didn’t particularly like them, and unintentional style leader that he was, he influenced a lot of other men to go bare-headed. An alcohol-inspired corollary to this theory says that when the president was killed, the hat industry was not overly wrought. Or Sam Giancana didn’t like hats. Or something like that.
  • But the hat industry has recovered. Instead of making items that were thoughtless accessories, like a handkerchief, hatters and milliners the world over have come up with new takes on headwear for protection, fashion, or both. If you can’t find a hat that suits you, try installing an imagination first. Then reboot. (Close all open programs, such as Boring 6.2 and the Stick-In-the-Mud suite.)
  • The fedora that adorned so many men’s heads before President Kennedy is a hard look to beat. Once Indiana Jones brought it back, it was off to the races. Wider brims are more manly. Ask anyone in my law school class, and they’ll grin (or grimace) and tell you all about my insistence on wearing a brown or grey fedora, back brim properly snapped up, with a grey London Fog raincoat. For urban swashbuckling, it’s the best. (Just don’t walk into the Recorder of Deeds and say, “It’s a worthless medallion, Marian. Are you gonna give it to me?” Trust me.)

    Bogie knew.

    Bogie knew.

  • Berets are super cool. Women wear them best. French men carry them off wonderfully, Spanish too, so much so that you forget they’re a stereotype. Seems to me thinner faces work better with them, but I don’t care. Hard to find any in this country that aren’t super-hot wool. When I go to Italy this summer, I’m going to get at least one in a lighter weight fabric. Oh, and colors are good. Except raspberry. Built like it was, that color had the nerve to ask me if I planned 2 do it any harm…
  • The most ubiquitous hat for men is, of course, the baseball-style cap. Not that there’s anything wrong with it! [Seinfeld hand motion] There’s a difference, though, between just grabbing the dirty old Caterpillar cap you’ve been covering your bad haircut with for months (unless you really do work on a farm) and actually choosing one that makes sense with what you’re wearing and looks good on you.
  • Baseball Cap Caveat No. 1: Don’t be one of those douches who wears a cap representing a team with which you have no connection, and then when a stranger smiles and exclaims “Go Pirates!,” shoots him a WTF? look. That’s jagoff stuff.
  • Baseball Cap Caveat No. 2: Backwards baseball caps are for 1) children under the age of 9, and 2) baseball catchers who are AT WORK. If you wear your cap backwards, you better be the second or you’ll look like the first. The intensity of your wrong-headed notion that you look cool this way only magnifies the fact that you do not.

    The Duke rocked this.

    The Duke rocked this.

  • I have achieved a sufficient gray-to-brown ratio in my hair to look distinguished in a homburg. Problem is, I do not live in a climate that would require the proper sober overcoat that must accompany it. Nor do I have any business serious enough to warrant the stony face I would have to wear under such a prodigious lid.
  • Will someone please explain wool stocking caps in 90-degree weather? Unless you’re Zach Brown, stop it. Even if you are Zach Brown, stop it.
  • That said, some younger guys can look good in the lighter-fabric stocking caps. But by doing so, they risk the completely reasonable third-party conclusion that they are lax about scalp hygiene.
  • Yes, I have a real straw boater. Yes, I sometimes wear it. No, my wife does not care for it, and checks my drivers license to make sure it says 1961, not 1921.
  • No man in a homburg wil evah surrendah.

    No man in a homburg will evah surrendah.

    Then there are bucket hats. She hates how I look in buckets. But for summertime golf or the beach, there’s nothing better. An unburned neck is sometimes more important than fashion.

A life without hats to playfully smack a friend with, to wring in one’s hands while waiting for important news, to wave wildly at parades, to refashion into rally caps in the bottom of the ninth, to tip to ladies…what fun would that be? So take my advice: put a lid on it. As many ways as you can.♦


Yes, it makes me look like a hyper-doofus version of Secret Squirrel. But I’m sun-protected.

© 2013 Adam Barr

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2 thoughts on “Thoughts on Hats

  1. Jim Teague says:

    Dear Secret Squirrel, er, I mean Adam,

    All excellent points.

    I’ve never been able to pull off a really good hat look. I always come off looking like someone who got lost in the MGM Studios dressing room. Something about the size of my head in relation to the rest of my body.

    BTW, I think the other time it’s okay to wear a baseball cap backwards is when you are taking photos. Otherwise the brim hits the camera when you look into the viewfinder.

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