Optimo Hats

Inspired by the founding partner of his firm, my husband Todd decided what he really needed for his winter wardrobe was a good hat. The founder of his firm has an impressive collection and offered to take my husband to “his hat guy” on the Southside. Apparently his puppy had gotten a hold of two of his hats and he needed to visit Optimo for a repair/replace consultation. Todd was so excited he talked about it for days. Optimo Hats is a bit of a Chicago institution and they did all the hats for the Johnny Depp movie Public Enemies. Located at Western and 102nd, they claim to be the “one of the last remaining traditional hat shops in the world.” Apparently Todd ordered a great hat. I wouldn’t know, I haven’t seen it yet (they are custom made so it takes awhile). But it cost $500 so it had better be awesome.

What I got out of the whole thing was an evening at Optimo’s Annual Holiday Party in the penthouse of the Blackstone Hotel. Todd borrowed a hat for the occasion, I was one of two hatless guests. The crowd was memorable: mostly men between the ages of 35 and 60, racially mixed and everyone dressed to the nines. We met a doctor, a millionaire and a retire Chicago firefighter, and everyone was really into their hats. Like they really wished they could pull off a porkpie, or they were planning the purchase of a panama for the summer. One man wearing a red hat and red suit explained that he bought the hat first and let it sit in his closet until he had the suit made to match. It was fun to see such a mixed crowd of people come together over such a specialized interest.

The owner of Optimo is a white guy in his mid thirties named Graham who purchased the store from the last owner, whose father had started the shop. Clearly identifiable as a hipster, Graham was ahead of the trend, learning the craft of hatmaking at sixteen when he apprenticed himself to the owner of Optimo. It is incredible that a sixteen year old had such clarify of vision, but indeed, he seems to have locked on to his trade early in life. I am looking forward to seeing Todd’s new hat. Turns out the founder of his firm’s hats were irredeemable. That’s an expensive puppy.