Stuff like this is so subjective. I agree that a lot of the things up for vote are certainly innovative and important in some form but not necessarily cool.Honestly, not many of these are cool. Some are nice, maybe ingenious or useful even. The runaway cool thing to me is the IRIS Circadian SkyCeiling.
My vote on the list would be for the Winnebago, but I'm with @deadeyededric that it should be Indian Motorcycles. Although I wish they still made Victory.