Since my legs are only two feet long (at best!) anyway...LOL...I could never wear boots regardless. I work in a bank and see lots of people who work outside on construction sites or whatever come in wearing boots and shorts...for comfort's sake. And chances are, they wouldn't be wearing the boots if they weren't a requirement! Yes, it does look odd but they don't care because again, it's for the sake of keeping as cool as possible.
For fashion....here in Redneckville, young girls think it's cute to wear Daisy Dukes and Red Wing boots or cowboy boots. Me? Not so much. On the flip side...and oddly, I guess...I do think a skirt and the right pair of boots CAN be cute together (ie., Julianne Hough in the new version of Footloose) but if I could pull it off, I'd never do it because like someone else said, I'd sweat to death!