“When I opened my first club at 22, I was also in my first year of law school. I really never had time to go home and change, so my unofficial uniform became jeans, T-shirts, kicks, and hats. Then I founded the Lookingglass Theatre Junior Board, and I met the actor Tony Fitzpatrick, who introduced me to Optimo Hats. Owner Graham Thompson is one of the last true, legit artisans of this craft in the world. When I became a regular on Windy City Live and the Today show, I learned that I needed a shorter brim so that the TV lights didn’t cast a shadow on my face, so Graham shortened the brims on the Stingy for me. I now have about five hats from Optimo. They are handmade, classic, and built for life, so I don’t need many.” From $495. 51 W. Jackson Blvd., Loop