An Optimo hat Credit: Richard A. Chapman/Sun-Times media

When I bought my beautiful brown-felt fedora from him a few years ago, Optimo owner Graham Thompson was still operating out of a combination storefront and factory on Western Avenue in Beverly, where the hat-making happened on premises. Things have changed. In 2016, Thompson moved production to a former firehouse on 95th; if you want to buy a hat, you head for the store at 51 W. Jackson, in the Monadnock Building.

The Monadnock, of course, is one of the most splendid things in Chicago. Optimo occupies a ground-level space in the 126-year-old northern half, whose 17 stories are supported at the corners by brick laid to a thickness of up to six feet. Stand across the street and contemplate its plain, perfect lines before you go in.

But do go in. Optimo general manager Tiffani Bell says the current owners of the building wanted to create an atmosphere of retro grace with their choice of high-end, small-scale, craft-oriented storefront tenants (a bespoke clothier, fine men’s footwear, no Starbucks), and Thompson was an early lessee. Designed by Angela Finney-Hoffman of the now-defunct furniture and design business Post 27, the front room of the store contains a long, absolutely clutter-free counter with a polished concrete surface and stools planted in the floor along its length. All the rest is dark wood, low light, glass, decorative hat blocks, and the hats themselves, displayed like artifacts in a gallery, on shelves consisting of two metal cables apiece.

Thompson has a gritty backstory reminiscent of the standard tale told about young white Chicago rockers from the 60s who’d spend their nights at south-side clubs, cribbing off black blues masters. His own master was Johnny Tyus, who made and sold hats at a shop on 79th. No grit here, though. The store is classy and smooth and full of the romance of fine things, and I felt like a hayseed on a recent visit, wearing the crushable straw I’d bought at Goorin Bros. for $60—which is to say, roughly a tenth to a 100th of the price for an Optimo. I saw fedoras, homburgs, top hats (Bell says a surprising number of frantic grooms show up looking for them on their wedding day), rolled brims, a Stetson-y thing, and even old-fashioned bowlers, in shades of brown, black, gray, blue, tan, and red.

The felt, Bell told me, is “wild fur, and specifically beaver-fur felt for about 95 percent of our hats. The others are blends of other wild furs and hare’s fur.” Felt finishes vary too, from flecked to shiny, “long-haired” Melusine. The straws are woven in Montecristi, Ecuador—oddly enough, the traditional home of the “Panama”—and sent in a dome shape to Optimo, where the crafting is done. A fine weave is more expensive but also less airy. I prefer the texture of a rougher weave myself. An astonishingly good salesperson, Bell had her tailor’s measuring tape around my head before I quite knew what was happening. The Goorin Bros. hat rested on the counter.  v