It's kind of a curious thing, isn't it? Here in Middle America, it has become way more acceptable for men to wear a wider variety of colors, and pink has become a favorite on the construction site. Maybe it's the Breast Cancer Awareness campaign that did it, but nobody even bothers to mention anything anymore if a guy shows up in a pink shirt, even if it's not Friday.
However, outside of equestrian circles, I do not see tall boots on men around here. With one exception: Latino laborers. Maybe not knee high, but they often wear their boots on the outsides of their pants. Plenty of men still wear cowboy boots around here, but always on the inside, and I doubt we've got any secret knee-high Luccheeses underneath there.