What If You’re a Man Who Wears Many Hats, But None of Them Fits Quite Right?

JUST A FEW of the many hats I’ve worn for various reasons over the years. As you can see, some fit better than others.


When my musical hero James Taylor started wearing a hat on stage a few years ago, I started thinking about covering my own bald head in public.

I always admired James back when he didn’t seem to mind letting his fans know he was losing his hair. Look at his album covers from the ’80s and most of the ’90s. Until his 1997 album Hourglass, JT didn’t try to cover his male pattern baldness, unlike, say, Elton John, Beach Boy Mike Love, Jim Seals of the popular ’70s duo Seals & Crofts, and countless cowboy-hatted country singers.

James’s lack of pretension when it came to his receding hairline was refreshing. It was honest. And it made his songs seem that much more true to life and heartfelt, to be sung by a man who apparently cared more about the depth of his music than the superficiality of his image.

Along those lines, I never trust any balding man who has the audacity to wear an ugly or cheap toupee, like televangelist and faith-healer Ernest Angley, or who sports a bad comb-over, especially really silly-looking or Aqua Net-dependent ones like Donald Trump’s perpetual swirly. Who do they think they’re fooling, anyway?

CAPS, VISORS AND HELMETS are optional head coverings for some men, though not always optimal for the follicly challenged.

But hats are different. They don’t just cover bald spots and unsightly scars, cysts or pump-knots on the heads of sensitive entertainers. The right hat or cap, worn the right way, can lend its wearer an air of whatever quality he wants to exude — sexy machismo, youthful rebellion, soulfulness, street smarts, country credentials, western swagger, or maybe just conformity, plain and simple, because every other member of that particular club wears a particular hat, too, as in a marching band.

Take Monkee Michael Nesmith, for example. No matter where or when the Monkees appeared — in winter snow or summer sun — Mike always wore a knit ski cap, even though he had a full head of hair. Why? Hmm. Maybe because he had unruly hair or protruding ears, I don’t know. But you get the idea. Mike, the quiet Monkee, seemed nice. And the cap made him stand out, at least among the Prefab Four.

My paternal grandfather was slick bald, as was my maternal great-grandfather. My dad and four of his five brothers — and probably one sister — were either bald or had “really high foreheads.” So I wasn’t too surprised when my own hair started thinning first at the temples, then on top, and then almost all the way to my collar in back. Fortunately, I don’t have a long neck. I was in my early 20s when the fallout began.

There was nothing I could have done to forestall the inevitable, as I started noticing that I was spending less and less time in the barber’s chair years before Rogaine went on sale. Also, the lady hairstylist who had always commented on the thickness of my sun-bleached, white-blond hair as she kneaded my scalp before brandishing her scissors soon began passing me off to the old guy with the thick glasses who reeked of cigarettes and specialized in buzz cuts.

I’d like to blame the ’60s-era football helmet that was part of my Salem Tigers Pee-Wee League football uniform in fifth grade for my early-onset baldness, or the motorcycle helmet that state law forced me to wear on the highway in my late teens (while riding my motorcycle, not in a car or bus). But, alas, my genes are to blame — and I ain’t talking about my Levi’s or Wranglers. That’s another story entirely.

So that’s why I’ve always been on the lookout for comfortable hats and caps to wear outside on sunny or even hazy days. Shoot, I can sunburn my scalp even on cloudy, rainy days like the ones we’ve been having lately. For that matter, I’ve also noticed that the tiny air holes in the top of a ball cap or the mesh back of a trucker-style cap can let in enough UV rays to burn my noggin in spots. It’s a sad situation.

But thanks to James Taylor, who, if his social media posts can be trusted, now wears a cap of some sort everywhere he goes indoors or out, on stage or off, I’m in the market for a good hat or cap to wear for any and all occasions, whether it’s at home, work, play or church. I ain’t particular. It just needs to fit my size 6-7/8 head and look like a million bucks.

Michael Reno Harrell, my second-favorite living singer-songwriter and favorite storyteller who looks good in hats even though he has great hair, once suggested that I get myself a derby — a black, not green one, I assumed — for Songwriter Nights at Brown Mountain Bottleworks in Morganton, where I used to play some of my tunes.

I was afraid to ask Michael why he thought a derby would suit me. Maybe because a round-topped derby or bowler hat would match my, um, well-rounded features? Or maybe because the mere sight of me in a derby would distract listeners from any sour notes I might sing or fumble-fingered notes I might play? Or maybe — and this is a stretch — maybe because I’d be so darn preoccupied by the thought and feel and warmth of that derby on my cold, bald head that I wouldn’t be aware of the audience and wouldn’t suffer my usual stage fright.

Heck, I don’t know. I’m open to suggestions.