The John B. Stetson Company was known for its iconic “Boss of the Plains” cowboy hat, but the once-giant American hat manufacturer produced styles for city slickers as well. Stetson’s advertisements for derbies, fedoras, panamas, and more led the trends of men’s headwear in the young century.
The bowler hat, or derby, was a working-class British phenomenon that eventually found favor with American urbanites. Before René Magritte and Stanley Kubrick turned the bowler into a symbol of oddity, it was a lid for commoners and the well-to-do alike.
The Stetsonian fedora was a darb of a choice of headwear for entertaining a young flapper in the Roaring Twenties. Just add giggle juice.
The sleek style of illustration — clean lines and minimalist composition — is so compelling you might not notice he isn’t wearing the hat. The ’20s marked the end of Stetson’s appeal to young men as the Great Depression warranted a focus on value.
Could a Stetson Playboy save your life? Probably not, but who could afford to take that risk?
Worldliness and culture was a defining feature of Stetson’s cultivated demographic. The chapeaus caught on, even if Esperanto never did.
A bizarre, passive-aggressive love triangle might seem an odd approach for selling a hat. Appeals to a man’s romantic life, career, and dignity were common sales tactics for the fast-paced urban dweller.
As the war captivated the attention of every American, Stetson found its customer base returning from overseas fighting. The “loose lips sink ships” adage is employed with an aerial twist.
The Stetson Stratoliner was a fine fedora to “bring him home in style” from the European front. Calls for patriotism and Americana were a surefire ad technique, too. You can still buy a Stratoliner, but the price has scaled from $7.50 to $175.
Celebrities Bob Hope, Bing Crosby, and Douglas Fairbanks, Jr. donned Stetsons for a seasonal 1948 ad campaign along with George Montgomery, Dick Haymes, and Dana Andrews. The movie star endorsements were sure to leave an impression on readers-about-town.
The only advertisement for Western-style Stetsons in the Post shows the cowboy hats in all their Southwestern glory. Ten-gallon or not, the cowboy Stetsons are archetypal of the brand.
Panamas and yacht hats made of straw were a light choice for summer wear, and the boater-style, Barford, was retro even for 1950.
The 1950s would prove to be the last decade for ubiquitous hat-wearing for American men and the last one in which Stetson could command the sleek look of urban fashion. Bowlers and fedoras eventually gave way to stocking and baseball caps or — shockingly enough — no hats at all.
Read “The Fall of the American Hat” for a closer look at the decline of the American chapeau.