In 1605, Guy Fawkes, the Englishman who fomented the Gunpowder Plot, encouraged his followers to wear the same tall, black sugarloaf-shaped hat that he wore. Aristocrats in feathered Puss in Boots-style hats expected men of lower rank to remove their hats as a sign of respect. These fops found Fawkes' followers appearing everywhere in big, black hats, which they refused to take off. It worked as provocation. Look, we’re still talking about it.
Benjamin Franklin's court appearance in Versailles, France in 1776 rocked the entire country. A city boy himself, Franklin entered court sporting a long-tailed furry Frontiersman's cap. His “look” popularized the American cause in ways Franklin's words could not accomplish. French people bought all kinds of touristy trinkets with his fur-hat portrait printed on them. Although neither Franklin, nor Davy Crockett, born in 1786, could profit personally without international copyright laws, it was just as well: Native Americans designed the originals. But the look caught on, and in 2025 you can still "be" Davy Crockett for a hundred bucks on eBay, or get Walmart's women’s version for $15.
A French person in 1799 could still buy a bicorne hat for the price of fifty
small cheeses until Napoleon Bonaparte wore his bicorne in public appearances. Then the price went sky high. Napoleon wore his sideways to make it easy for people to
spot him in a crowd. During battle, an added-on gold band helped troops see him better. The band, Cock-Starkey suggests, caused the hat to resemble an emperor’s crown. Talk about subliminal branding. Bonaparte owned 120 bicornes at his death. One that still carried his DNA brought in $500,000 at a 2018 auction.
Let's fast forward to the 1850s. Why would a 6'4" man choose to add 8 more inches to
his height? Abraham Lincoln used his stovepipe hat to store papers and speeches to "fish out" when he needed them. The one he wore the last night of his life is part of a popular
display at the Smithsonian. Keep that under your hat in case it makes Trump
jealous. Or has it already?
Iconic photos
from 1906 show President Teddy Roosevelt personally digging out the Panama Canal. Poses of TR running a steam shovel or
shoveling dirt at the ground-breaking on the Panama Canal don't seem over the top to those of us who've watched a president pretend to know how to drive a garbage
truck or shovel fries at McDonald’s. Teddy’s photos got him credit not only for “building” the Panama Canal but also for popularizing “the Panama hat.” The hat in the photos was actually made in Ecuador—there's one on the head of every working stiff in
the steam shovel photo. Having the hat on at all may have been a happy accident. I can imagine Roosevelt’s public relations person saying, “Grab one
of those guy’s hats before we take the picture—Teddy’s forehead’s all sweaty.”
My
annoying AI buddy, Gemini, wants me to add that “the hat’s black band symbolized
Roosevelt’s solidarity with the Ecuadorian president, a champion of equality,
progress, labor rights, tradition, culture, and sustainability.”
Who needs a PR guy when you've got Gemini? But I get it. Masters of self-promotion understand that hats can be brands and branding is powerful. A picture really is worth a thousand words. My friend Rex, who recently returned from a four-day cruise, brought back a paper “Bermuda hat” made in China. It certainly makes him look like he spent more than a day and a half in Bermuda.
Winston Churchill claimed that his signature homburg hat, first worn in the 1940s, gave photographers something distinguishing to focus on. Apparently, his bland face didn't read as “Here I am over here.” The hat made history, and one from his large collection brought in $11,750 in 1991.
I
passed a advertising billboard in Tennessee last month alerting me to the exit for The
Trump Megastore. A recent iteration of President Trump’s iconic red ballcap
proclaims, “Trump Was Right About Everything.” It will, no doubt, be sold with other versions
of the cap in the megastore. Why
wait to auction off one's memorabilia when, like in Guy Fawkes' scheme, you can get lots of people to wear them right now, right along with you? China can
mass-produce cheap knock-offs of the official 'Made in the USA’ hat—before
tariffs, they were made for $3 and sold for $14; after tariffs, they're made for $3 and sell for
$20.
Hats pay off. Leaders who don caps make history—if not for being
right all the time, then for making sure they’re seen.
