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Chris Lake

After the automobile became a common possession in the mid-20th century, fewer gentlemen spent time outside, and hats became less of a necessity. But Chicago’s Optimo Hats is trying to change this, one fedora at a time. Tucked into the heart of the city’s downtown Loop amid the Chicago Board of Trade and similar century-old institutions, the brand-new (yet timeless-looking) shop appears as if it opened the same year as the landmark 19th-century Monadnock Building in which it’s located. All things considered, though, it’s completely appropriate, given how this throwback is bringing fedoras, porkpies and bowlers back into fashion.
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al oliver
If John Dillinger couldn’t shop here, Johnny Depp certainly has. Owner and hatmaker Graham Thompson, who’s been making custom-fitted, handmade men’s hats in his original South Side store for nearly 20 years, made all the toppers used in films like Public Enemies and Road to Perdition with Tom Hanks. To top it all off, he’ll be topping off Depp once more in his upcoming film, Dark Shadows. 320 S. Dearborn, www.optimohats.com