Optimo Fine Hats: Classic Americana.

Graham Thompson’s friends in high school thought he was crazy. He would frequent Johnny’s Hat Shop on Chicago’s South Side, not the sort of place teenagers typically spent their free time. But Thompson was an old soul trapped in a young man’s body. He loved not only the idea of wearing dress hats—something he picked up from watching black and white movies with his father when he was younger—but the people who wore them as well.

“I was drawn to everything about it,” Thompson says. “I thought Johnny and his shop were the coolest thing ever. And his clients! Old blues guys, businessmen in suits, the locals from the South Side. It was special.”

So when Thompson graduated from college and returned to Chicago, the first thing he did was ask Johnny to make him a new hat. “He told me it would be the last one he could make for me, because he was retiring,” Thompson recalls. “I was so sad. It was this huge part of Chicago’s heritage. So I took it over.”

Now Optimo Hats carries on the time-honored hat-making tradition in the same South Side location where Thompson apprenticed. Although he had to learn how to operate the decades-old machinery, it only added to his appreciation for classic, stylish headgear.

“I got into this business [in the mid-1990s], when appreciation for dress hats was at an all-time low,”
he says. “But even then, the fewer people that wear something, the cooler you are if you wear it. And now that such classic styles are back in fashion, it’s not like a pocket watch, an affectation that doesn’t make sense in modern times. It makes sense to wear them. Not wearing a hat when it’s cold out makes as much sense as not wearing sleeves, and wearing a ball cap or cheap wool pullover with a nice topcoat makes as much sense as wearing tennis shoes with a suit.”

All of Thompson’s tools and machinery were made in the 1930s and 1940s, when hat-making was a big business and heavy demand resulted in a high mark for quality in the industry. The process hasn’t changed much. It starts with using the best material—wool is most common—and making sure it’s milled correctly. The material is then steamed, blocked (shaped), ironed, and shaved (sanding the crown). Thompson compares it to cutting a diamond—putting a fine finish on the hat through abrasive and polishing technology.

Thompson has a steady clientele of classic chapeau lovers, but he also sees people in his store every day who are new to dress hats. He says even novices can spot quality as soon as they hold it in their hands, well before experience tells them a well-made hat repels water, gets softer with age, is more durable, and fits better.

“Hats are just a classic piece of Americana,” he says. “What will America be remembered by? Its great jazz, automobiles, and classic American style. Great hats symbolize that.”