I shopped for many months for the "perfect" motorcycle boots. I had a new Harley and wanted to look the part of the motorcycle chick but I just couldn't find a pair that was comfortable.
I ended up getting a very comfortable pair of hiking boots then dressed them up with a set of Willie G skulls in the laces.
I'm definitely more concerned with comfort than looks and my thoughts are that you should wear what is comfortable.
What do you wear?