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…
