David - Union Square, SF
"Growing up I loved watching I Love Lucy, and I think I like the '50s. So I [frequently] wear a bowler hat and sometimes wear a top hat. I like to clash with different styles of when I was growing up, just to make it it my own unique style. Like, wherever I go I have something from where I've been."
Not just the bowler hat, but the checked button down and the scarf and ribbon (resulting in multi-pattern mixing) caught my eye. The bright colors remind me a bit, of the people in Bolivia and Peru who wear bowlers with their bright native dress (see below). Good job David, not many guys go out on a limb, glad you did.
Battered modern loafers.
Indigenous Bolivians wearing bowlers.