Chicago’s Hat Culture


Goorin Bros.

Our always fashion-forward concierge contributor Philippe Gills share the best places to get fashionable hats for the fall months in Chicago.

Walk down any well-populated street today in Chicago, you will see the predominant style of hat worn probably has a soft rounded crown with a stiff peak in front, ‘custom fitting’ courtesy of a plastic or Velcro tab in the back; and the name/logo of your favorite sports team or company. Sport one with a circular brim these days and your likely to elicit curious stares from strangers impressed with your bold choice.

Based on the above, it’s hard to believe we were once a city obsessed with proper hats. Archived photos of Chicago and its inhabitants over the last 100 years prove this, with countless shots revealing a sea of brimmed elegance of every shape and style cutting across all socio-economic classes and worn by everyone. During this period there were dozens, if not more, hat makers based right here in Chicago with the sole purpose of covering your head with style.

Quickly coming to symbolize status, it’s hard to fathom that proper hats origins placed them on the heads of the most common of person. For example the top hat that we associate with Abraham Lincoln was actually worn by commoners. The fedora? It was worn by everyday Chicagoans regardless of status, not just Hollywood stars like Humphrey Bogart or gangsters.

Although proper hats fell out of style for the most part in the 90’s, they have since returned to the ‘must have’ section of our closets, thanks to several well placed sightings on the heads of stars in film, music, and beyond. So who’s got the hat goods?

Three spots stand tall in continuing the Chicago tradition by covering thousands of heads in every style imaginable. I am drawn to each one because they offer more than hats themselves, are able to help you sift through dozens of styles, and all feature basic fitting.

Sids Clothing & Hats, 609 W. Roosevelt St.

I can only imagine who has walked through their doors of this brim time machine, open since 1969, with Maxwell Street and its bluesmen playing in the street nearby on weekends. Think classic styles, and iconic brands like Dobbs and Stetson with warm experienced personalities to match.

Goorin Bros Hat Shop, 1533 N. Milwaukee Ave.

Don’t be fooled by the hipster address, Goorin Brothers has been punching out hats since 1895. They feature a vast selection with several hats, reasonably priced, all with the Goorin logo present. This is a cool spot for fans of Goorin, hipsters, and those somewhat new to the hat game who want classic styles with a modern twist.

Optimo Hats, 320 S. Dearborn St.

In short, crème de la crème. You don’t simply want to buy a hat, you want to own the process, customizing from top to bottom, limited only by your imagination. Graham Thompson, master hat maker, hard-core Chicagoan, and owner of Optimo Hats, is a true throwback to the days of yore by using classic by-hand technique and materials. Jaw dropping in their commitment and attention to detail; Optimo makes you truly appreciate the culture of what wearing a hat really means. Optimo hats are not average priced but then again, neither are their hats. Par excellence!

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