Skateboard shoes, all the way! Being an anti-establishment, but somewhat successful businessman, I like to wear whatever I want, no matter what anybody else is wearing. Believe me, you DO have an advantage at a real estate auction if you show up in a beat-up Toyota 4x4 wearing holey Levi's and skater shoes. However, if I'm going to a function where friends or family will also be in attendance, I will conform to whatever the expected attire is. That's only out of consideration for my friends or family though, so they won't get embarrassed by my being with them.
Charles