At Chicago’s Optimo, men’s hats are more than an accessory—they’re an entire way of life.
There was a time, not that long ago, when every neighborhood had its own milliner. In the 1930s, 40s, and 50s, when hats were a man’s defining accessory, customers demanded the finest materials, the perfect fit, and the most fashionable profile. Business was, therefore, robust.
Today, only a handful of these outfitters remain. But in Chicago, one notable outlier is keeping the craft of men’s custom hatmaking alive. Housed in a modest building on the city’s South Side, it has a façade that displays just six black letters: optimo. Inside, dark walls and countertops are lined with some of the highest-quality hats you’ll find anywhere: creamy straw panamas, precision-cut fedoras, and sharp, narrow-brimmed trilbies.
For two decades, owner Graham Thompson has supplied a clique of committed hat wearers, some of whom have crossed continents to be fitted in person. On entering the shop, clients are carefully measured by staff (Optimo offers a rare three head sizes between each standard size) before embarking on a consultation that takes into account their personality, lifestyle, and wardrobe. “A great hat absorbs the character of its wearer, the way well-made things tend to do,” Thompson said. “We want to sell hats that will become part of who a person is.”
Once a design is chosen, the real work begins: at Optimo, proportions are refined using vintage molds, shapes are strengthened by a steaming process known as decating, and silk linings are folded and stitched by hand—methods long since abandoned by most modern hatmakers.
A Chicago native, Thompson grew up idolizing actors like Jimmy Cagney, Robert Mitchum, and Orson Welles. His love of that old-world aesthetic delivered him, at age 16, to a local hatmaker called Johnny’s Hat Shop. He apprenticed under late owner Johnny Tyus and eventually bought the business.
That was 20 years ago. Today, Optimo Graham has clients everywhere from Iceland to Australia. Jay Z and Tom Ford are fans, and Thompson has made hats for films Chicago’s including Public Enemies and Quentin Thompson of Optimo at his store on South Side. Tarantino’s western, The Hateful Eight. Nonetheless, the operation remains small-scale. Optimo recently opened a new factory in a former fire station, but has otherwise limited its growth to a second showroom downtown. “We’re not in a rush to expand,” Thompson said. “We don’t want to be the biggest hat company in the world—just the best.” Hats from $450.