Context is everything. It's easy to say "just do it" but that may not be the reality.
If you're doing it in an environment where it seems strange or unusual, then I'd say don't do it unless you're okay with the added attention. If it's something other people do and you just don't have the nerve to do it yourself, then I'd say you should just do it.
For example, if you live in an urban area and everyone else is in dressier attire, you would stand out. If you're in a smaller town and it's not too unusual for people to wear tall boots on the outside, then you'd be just part of the crowd.
If you wear flashy boots, you're gonna draw attention either way. If you ride a motorcycle and wear a leather jacket, holding your helmet, it wouldn't matter really where you are and people wouldn't think much of it.
It's context, right?
: if i only had the b**ls to wear tall boots out in public with pants tucked in but i get in car wearing them that way but as soon as i get in public off they come what im i afraid of your thoughts would help