I guess I'm pretty oblivious to cigar smoker stereotypes.
There's not a thing wrong with riding a harley, or even with having brand associations. I'm talking about people who think they can buy a "lifestyle". They do it through harleys, jeeps, gibson guitars, expensive cigars, nike air jordans, or anything else they think will help people recognize what "type" of person they are based on their status purchases.
I don't think it's wise to try and apply those traits on an individual basis though. It's too difficult, and it leads to a cynical outlook. In other words, I would never assume that just because somebody rides a harley, they are trying to buy a lifestyle.