One Man’s Hunt for the Perfect Newsboy Cap

Which is when I heard, “Hey there, Tex….”

I turned around, despite never being called “Tex” in my entire life. The old timer is looking at me in the mirror, not even bothering to turn around. Still, the initial thrill from that nod is buzzing through my body. Is he about to buy me a beer? Ask me to sit down and take a shot with him?

“It’s on backwards.”

I didn’t understand, and I said as much. “I’m sorry?”

“Your cowboy hat, Tex. You’re wearing it backwards.”

Somehow the old-timer’s laughter expanded to fill the entire bar, despite it being outdoors. A few of the bartenders caught the whole exchange, and proceeded to call me “Tex” for the rest of the night.

Needless to say, the cowboy hat didn’t stick. But the idea of a hat? There’s still something appealing about it to me. Like dipping your toes into the shallow end of the fashion pool, without fully jumping in. A few years had passed since the cowboy hat incident, and I found myself thinking of hats as an entryway into style once again. I thought about who I looked up to when I was growing up. Robert Redford. Paul Newman. Butch Cassidy and the Sundance Kid is still my favorite movie (which probably led to the situation in Houston, now that I think of it), but up there for me as well is The Sting. Redford in the floppy, slightly oversized newsie cap. Newman often rocking caps in a similar style both on and off the screen.

But before there were movie stars, there was my father, and before him, his own father. Both 100% Irish. Both often wore wool flat caps, which means I also tried to pull off this style of hat at different times in my life. Ten years old. Fifteen. Nineteen. Twenty-two. Twenty-eight. Thirty-two. Always just a stolen hat from my father’s closet. It never worked. I always put the hat back after trying it on. To be honest, I spent most of my life doing my damnedest to not seem like either man, but I think I finally might be old enough to pull one off.

Which is how I found myself in London looking for the perfect hat—trying not to think about what my Catholic, IRA-supporting grandfather would make of my spending money on the wrong side of the Irish Sea.

The popularity of flat caps amongst the working class, both in the UK and in Ireland, can be traced back to an Act of Parliament passed in 1571, which required all males over the age of six but below the rank of “gentleman” (i.e., excepting “maids, ladies, gentlewomen, noble personages, and every lord, knight, and gentleman of twenty marks land”) to wear woolen caps, described as “a cap of wool, thicked and dressed in England, made within this realm, and only dressed and finished by some of the trade of cappers,” on Sunday and holidays. Commonly called the “Cappers Act” or “Cap Act,” it was a thinly veiled attempt to boost the lagging British wool trade, and carried a fine “upon pain to forfeit for every day” one didn’t wear a cap.