One day, as we were descending into the subway in New York City, we saw an older gentleman coming up the stairs. With our view from above, we could see an absolutely horrifying splotch of skin cancer right in the middle of his big bald head. It was quite memorable, and somewhat terrifying. Since that time, Sara has insisted that I keep my own big bald head covered whenever I go anywhere near the sun.

It certainly beats rubbing sunscreen into your hair. However, sometimes I feel kind of dumb wearing a ball cap.

When I was in college, I wore a ball cap practically every day. Maybe that’s why I feel like maybe I’m a little old to be wearing a ball cap. Or sometimes I feel like I’m dressed up a little fancy to be wearing a ball cap (and by fancy, I mean a button down shirt or something, I’m not exactly walking around in a tuxedo here). I don’t know, maybe it’s true, maybe it’s not, but in any case what are my other options? I’ve tried on a few other kinds of hats here and there, but none of them seem quite right. Is there an accepted “adult” style of hat? What kind of hat fits my personality?

I could go with the hiking hat, but that’s pretty much as casual as a ball cap, and I don’t want to imply I’m an outdoorsman.

What about a bahama hat? Still pretty informal, but more suitable for relaxing in a cafe in Havana, which is more my speed.

Or perhaps a panama hat? A little more formal, and it sort of looks like the kind of hat I could grow into, like a gangster, or Wilford Brimley.

I don’t know. They’re all a little casual without being too casual, which I like, but maybe we need to expand our search a little bit. Consider some alternatives.

I don’t think I could do a cowboy hat. I’m not exactly country, and I’m not sure it would really fit in in my neighborhood.

On the other hand, maybe a newsboy hat. Oliver looks pretty damn good in his, why not me?

Not too bad, but maybe we need to think outside the box a little bit…

Barbershop hat?

Okay, but if I’m going to go barbershop, why not do it right and go porkpie?

I think the best looking one has to be the fedora. Great color, feather in the brim, jaunty angle? Check, check and check.

As long as we’re going old school, maybe I should go bowler hat. A little old fashioned perhaps, but also a little cool, steampunk style.

Now we’re talking! Or maybe something like:

Hey, if it’s good enough for Indiana Jones, it’s good enough for me!

Or, of course, there’s always the ever popular…

So, gentle reader, what say you?