I work with three guys who are at least semi-serious runners. I think all of them have done at least one marathon, and they do shorter long races on a regular basis. Get all three of them together, and the talk soon turns to this running shoe vs. that running shoe, what do you use for heart monitor/GPS, etc., etc. The reason I bring this up is because somehow they got talking about leg shaving one day. Evidently, some runners shave their legs. All three of them think it's ridiculous. One of the guys said, "C'mon, you're not a swimmer! You can't tell me that a little bit of hair is going to create that much drag at speeds we can run."
Then they got into talking about how some guys will show up at a race with stubble on their legs, like they forgot to shave for a few days. I, not being a part of that conversation at all, quipped dryly, "Yeah, I hate it when that happens." They laughed, but had no idea why I thought that was a humorous thing to say. Don't get me wrong, even though this particular group of guys doesn't know me outside of work, I never got the impression that they were ridiculing a guy for shaving his legs. They were ridiculing any perceived performance gains, much like Shyheels feels about guys who remove decals off their bicycles.
In order to tie this all back together, I'll repeat what I said before--It's perfectly acceptable for any guy to wear tall boots if there's some perceived practical reason for it. I think we got off into this leg shaving business because the attitude is pretty much the same. Of course, it's all ridiculous and subjective. Why do body builders shave pretty much their entire body, and that's just fine, but if I did it, I'd be really strange.