Man I can't beleive I never saw this thread! I've been ridin since I was 10. Started out on dirt bikes so long ago but also ride Harleys now days!
I own a 2007 Harley-Davidson Dyna Street Bob. I wear a leather jacket and chaps when its cold outside other than that its tank tops and lite wait pants, sometimes shorts and since I live in Cali, a skull cap!

First pic is when I bought my Harley in August of 06

Second is how it is know minus the saddle bags. I'm gettin ready to ride to Sturgis this year with my uncle. Its goin to be a blast. Man O man I can't wait!
 
Keep the wheels burning