The Mad Hatter

My wardrobe genetics come from my parents. My mom is elegant and graceful, while my dad will occasionally tuck his sweatshirt into his jean shorts. I fall somewhere in the middle.

For years I was on my own, free to pick out any macabre combination of menswear. I decided early on that I would not pay more than $20 dollars for any individual piece of clothing. That led to a thrift store phase, a wear-it-till-it-disintegrates phase, and a punny t-shirt phase. Nothing says cleverly fashionable like "Virginia is For Lovers" written in comic sans across your chest.

Now I have a wonderful girlfriend who has made it her mission to turn me from Frankenstein's monster into a cultured, sophisticated man about town. Out goes my sleeveless Black Crowes license plate t-shirt from 1998. In comes Hugo Boss. From the neck down, she can dress me however she pleases.

From the neck up, though, I still retain editorial control. Hence the fedoras. I bought one last weekend during a trip to Charleston, South Carolina. I furrowed my brow as I tried on porkpies, derbies, homburgs and bowlers before settling on a nice earth-colored trilby. I asked Girlfriend to comment on each one. She mostly stood here, silent and horrified.

Any sort of men's hat that's not a baseball cap has supposedly been out of style since 1961, after JFK became the last president to wear a top hat to his inauguration. Since then, it's been seen more as a costume accessory than an actual functional piece of fashion. I was encouraged to see Matt Lauer wearing one this morning on the Today Show, at least until they started putting up pictures of Don Draper to make fun of him.

I went looking for answers. InStyle said yes, fedoras are back in style. For women. Drat. "The truth is, 99% of all white men look ridiculous in these," writes somebody named Isabella Snow. "We’re talking the equivalent sex appeal of maybe Ed Norton from The Honeymooners." A highly trusted source, Jenn Grabenstetter of Charlotte Magazine, told me this: "There is no fashion advice more enduring than this: Just Say No To The Fedora." Ouch.

So where, exactly, are all of us guys getting the big idea to wear these things? A few weeks ago, two friends of mine were running around wearing fedoras, and looked disappointed when I showed up unhatted. Movie stars wear them. Frank Sinatra wore them. Humphrey Bogart wore them. I love old black and white films where men run around in trenchcoats and fedoras and tip their caps to women as they walk by. I'm not sure if any women would see me do it now. They'd probably be laughing too hard.

Girlfriend probably has a point about my hats. I still have a full head of hair and there's no need to cover it up. And besides, by the time I go bald, I'll probably be tucking my sweatshirts into my jean shorts anyway, and by then, you'll be way too mortified to notice whatever it is I'm wearing on my head.