Hats Off to the Old and the Stylish

Nobody wants to grow old, but there are some upsides to it. I’m looking forward to several benefits that will come when I hit 70. For example, I will be able to wear a fedora. Laws vary from state to state, but generally, the only people under 70 years old who are allowed to wear these hats are hipsters, jazz musicians, and pretty-boys in J. Crew catalogs. Nerdy kids trying to look like one of the above can also wear them, but that won’t work for me; I gotta be authentic.

I can select almost any baseball cap and own it. I wear the dickens out of those, and they seem right at home on my head. Ditto a boonie hat or a floppy cotton bucket hat for shade when I’m engaged in outdoor activities. Fedoras are different. Worn as a lifestyle accessory—i.e., for no practical necessity—these hats would seem totally phony on me, or would at least feel that way.

Dapper gentleman Tom Wolfe gives more thought
to his handkerchief than I give my entire outfit.

Part of the problem is that I don’t have the rest of the wardrobe to match. When I dress in the morning, I go to the closet and grab whatever is clean, relatively un-tattered, and more or less appropriate to the weather. I have a remarkably small wardrobe budget. This is by choice. I prefer to spend my money on stuff besides clothes. Most days I end up wearing an old pair of khaki chinos or Old Navy jeans, a cheap flannel or cotton-poly blend button-down shirt (or an even cheaper T-shirt) from the clearance rack at Kohls, and whatever shoes REI had on sale three or four years ago, when my last pair wore out to the point that Mrs. Christensen wouldn’t allow me to go out in public with them. Also some socks, usually. Suffice it to say I’m not what you’d call “well put together.”

Getting back to my point, do you see how it wouldn’t look right to add something like a nice fedora to my ensemble? When I’m an old geezer, however, I can don whatever I want: powder blue jumpsuit, stained yellow western shirt and baggy tweed slacks, or an orange and purple nylon warm up suit. It doesn’t really matter. I can wear a fedora with any of it, because our society gives seniors a pass on these matters.

My whole reason for wanting a fedora is kind of ironic, given what I just disclosed about my personal style, or lack thereof. I’m into hats. I love (almost) all kinds of men’s hats. I can tell you the differences between a trilby and a homburg. I can describe in correct terms the design, usual materials, and even a little history of the derby, pork pie, top hat, and ivy cap. I don’t own any of these because, like I said, they just wouldn’t look right on me. But I like the idea of owning and wearing them. I bet I’d make a good haberdasher. Could you use some help picking out just the right headwear to go with your tailored suit and Italian leather shoes? I’m free for about the next 30 years.

Me, in 2055?