A hand-sewn hat from Optimo Hat Company

Finding bespoke men’s hats has become as rare as spotting a banker in a bowler. No wonder people travel from as far as London to visit Optimo Hat Company. “We have a lot of customers flying into Chicago just to see us,” says owner Graham Thompson.

For the past 16 years, the only brick-and-mortar outlet for the company’s fedoras, pork­pies, and other hand-sewn classics was its combined workshop and storefront in Beverly, 15 miles south of downtown. To better cater to fans—both out-of-towners and locals—Thompson plans to open an Optimo shop on the ground floor of the Loop’s historic Monadnock Building before the year ends. While the South Side operation will remain open, the new site will be a centrally located outpost for custom fittings and sales.

The relevance of the Monadnock’s authentically old-school vibe isn’t lost on Thompson, and neither is the building’s guy-friendly lineup of tenants—including a barbershop, a sandwich counter, a coffee shop, and a bar. “We’re going to use the building to stall our customers when we’re busy,” says Thompson. “Have a drink on us, and we’ll get you when we’re ready for your fitting.”

GO 320 S. Dearborn St.; optimohats.com

Finds Hand-sewn classic hats in high-quality felt and straw


Photograph: Chris Lake/courtesy of Optimo