Editor’s note: The following “Best of Boston” column was originally published Aug. 11, 2023.

I am probably the absolute last person to write an essay on dressing up. Except for a gorilla suit and my cherished Wilt Chamberlain No. 13 wife-beater basketball jersey, I could easily go the rest of my life with three pairs of denim ranch jeans, matching three snap-button blue denim Western shirts and a red T-shirt underneath for pizzazz. Oh. Throw in underwear, socks, $1,200 cowboy hat, boots and a barn coat.  

A cultural alarm ding-a-linged for me years ago. That’s when men started donning clown shorts that weren’t really shorts, per se. They ended mid-calf, giving the wearer a most comical suntan line. These mini-pants were adopted from the inner-city gang look, which came from those serving 15-to-life in the pokey. In a blink, CPAs and corporate attorneys were wearing the ghetto-strut pants-ette that oft exposed hairy butt cracks. (Band name.) Did it make the wearer look like Clown No. 4 or room-temperature IQ 11-year-old lookout on a Stingray bicycle in a drug deal?  

Yes.  

Did it stop brain surgeons from wearing this idiotic fashion statement? No. 

When did we guys start dressing like extras in a Mad Max movie? I’m guessing it was in the 1960s and it probably started quite innocently with the baseball cap. 

Prior to the ’60s, men wore fedoras or snappy, small-brimmed straw hats in the summer. In the late 19th century, men wore hats to shade themselves from the sun and also as fashion statements. They were also symbols of social distinction among men. When I was a kid, you didn’t wear a baseball cap unless you were a grease monkey, the Maytag repairman or batted behind Joe DiMaggio. 

Farmers might be to blame. In the 1930s, they started wearing caps with artsy fertilizer company patches. I still own an old John Deere tractor topper I’d defend with my life. Still. Back then, a hat with a logo or message was way too bold, too strangely counterculture for most. Somehow, in a blink, everyone’s wearing baseball hats. Even women. In the early pages of my lifetime, you just never saw a woman wearing a baseball cap. It would be considered — well. Like you were the overly muscled third basewoman on the all-girls and gravel-voiced Love That Knows No Name Bakersfield softball team. 

It was around the ’60s when we started advertising who we were on our caps and T-shirts. Well. We advertised not so much who we were, but who we wanted to be. 

Much as I ride horses, can’t play polo. Well. Adeptly. That doesn’t stop several million squeaky clean yuppies from donning snooty Ralph Lauren baseball hats with the polo player logo. It sends the message, “I Am Athletic, Master Over Large Animals & Effortlessly Rich.” 

Strange thing? No one stops these people in malls or grocery stores, yanks their caps off by the brim, slaps them lightly and announces: “No. No, you’re not…” 

As evidence of a life not lived, I read several interesting papers on the social status and history of hats. “Hat tipping” is steeped in the elaborate custom of doffing one’s head covering in deference to someone of a higher social caste. Or, to a lady. While men’s hats, like the old mountain cave bear skull, were symbols of social status, women’s hats were symbols of conspicuous consumption and badges indicating rank. It’s not like being silly is a brand-new aspect of the human condition. In the 19th century, men sometimes wore their big old hats — INDOORS — all day. Funny, too. Male hat fashion usually rose from the ground up. For example, the round black bowler hat was, and still is today, a symbol of British bourgeoisie. But the Charlie Chaplin bowler started in the mid-19th century as a working-class helmet of hunters and groundskeepers.  

A hatless man, way back when, was rarer than a brontosaurus. Every guy wore a hat. Or, a fly-attracting animal skull. With feathers. We live in polarized climes and today, the message you sport can scream volumes, from Oakland Raiders deviant to “Proud Grandma.” 

What kind of knucklehead-ette would advertise something like that? Aren’t grandmothers, by nature, supposed to be proud of the family tree that skips a generation? I confess. I’d like the shake the hand of a grandma wearing “My Daughter’s Eefus is Currently Rotting in Penitentiary For Perversion Against Small Animals.” Cripes. That’s like 94 letters and spaces. That’d set you back like $200 getting said hat embroidered at the mall. Plus, it would be an exercise in futility as the message going out to the world would be in prescription-bottle-sized type. 

Forget Climate Change. The demise of America will come from wearing prison shorts with beer bellies plopping over them. We don’t so much look into people’s eyes anymore but rather, at the small billboards that shade their noggins. 

I must confess. I’m guilty of donning a cap with a put-up-your-dukes political message. A while back, 80% of our weasly Not-So-Much local paper-shuffling social justice warrior donkey girl scouts high school trustees abolished our noble and cherished Indian mascot for Hart High. The craven little weenies.  

A pal of mine recently gave me a baseball hat with “Hart High Indians” embroidered boldly in front. I wear it to the local Piggly Wiggly in hopes that I may bump into one of the woke district cowards. I probably wouldn’t lightly slap them upside the head with my chapeau. I live in Los Angeles County where it’s the only felony that comes with a lengthy prison sentence. But, I’d give the unlucky trustee my best backwater evil eye. I’d wave my hat in the air, then commandeer the grocery store’s PA system to announce: 

“Price check on craven little weenies, Aisle Six …” 

Hm. Craven Little Weenies.   

I think that was the name of the band that played at Saugus High’s last prom or the logo for my next fetching baseball sombrero… 

The hat-wearing John Boston is Earth’s most prolific humorist and satirist. Visit his website, johnbostonbooks.com, and instead of back-to-school clothes, buy, for yourself, your kin and your children, his books.