Freddie has always been a fan of hats. Whether its a perfectly worn in baseball cap during a day at the beach or a crisp felt fedora out on the town, a well made hat would not go unnoticed in his hands. This month’s DVD release of the Chicago-loving, gun-wielding, historically inaccurate Public Enemies got us thinking, and got us a phone call from Freddie. “Those hats are from Optimo,” he said. Knowing that director Michael Mann was an accuracy buff (interesting, considering there were more than a few falsities in the story), Freddie knew the hats were made in Chicago, probably at the closest source to where Dillinger would have gotten his. This means only one name, Optimo Fine Hats.

Beautiful felt, fur, and straw bowlers, trilbies and fedoras used to be more prevalent than a bare head in major cities across the country. This was the time of three piece suits and people dressing up to go to church, so can we really be surprised that the trend has faded? What we cannot stand, though, are the pathetic versions of fedoras and trilbies put out by every Hurley and Abercrombie and Fitch under the sun. The fact remains, though, that a beautifully made hat is a thing of reverence, and there are fewer and fewer places to get them around the country. Borsalino has provided Freddie with most of his beautiful hats, but if he wants to stay domestic, there’s only one place to go. When you want the real thing, the place we can guarantee will have everything you need and more can be found on Chicago’s south side.

Now we know that Chicago may be a bit off the beaten path for many, but we believe that no matter what, a trip to the windy city should be on your to-do list. While you’re there, you may as well take a day out of your trip to go down to the south side and to Optimo. This place is the way things used to be: No flash, no fuss, just some great old timers and a few young enthusiasts making hats the old-fashioned way: by hand, one by one. Now no one said these beautiful articles would be cheap; they run from a a couple hundred up into the thousands. Think of this purchase, though, in the same way you would a heavy overcoat, or a great watch. Its something you can have for years, and with proper maintenance, could last a lifetime. Proper maintenance in this case means simply sending the hat back to Optimo once every few years for a brush up, with normally runs less than a hundred bucks.

You are able to order pre-made beauties from Optimo, but going along with all things traditional, this is done over the phone, once you have answered a multitude of questions, and possibly even taken a few measurements. While they will happily accommodate all phone orders, they too believe that the best way to get your beautiful new hat is by visiting the store. Give them a few weeks, and your beautiful headwear will arrive at your door neatly wrapped in a hatbox.

So if you’re tired of cheap fedoras with horrible skeletons and elastic sweatbands (we’re going to be sick), do the right thing a book a flight to Chicago. Enjoy the beautiful city, enjoy the south side, go to Optimo and then stop by Harold’s Chicken Shack, the fried chicken institution. We believe that a beautiful Optimo resting atop a man’s head is as close to a crown as we at FreddieBlack could think of, just ask Johnny Depp, who ordered five of his own after making Public Enemies.