I used to wear cowboy boots a lot with bootcut levis etc during the garage rock revival of the early 00s (see bands like Jet and the Datsuns for further evidence).
I used to wear Beatle boots a lot during the garage punk and acid rock revival of the 80s (see bands like Chesterfield Kings, Plasticland for further evidence). Anyone wearing cowboys boots would have been pointed in the direction of, I dunno, INXS or something. You gotta ask yourself, would Billy Childish wear cowboy boots? Would The Mummies? No. I still can't get over garage rock.
I've always liked cowboy boots- worn discreetly under good jeans and worn in they can look good.
No they can't. To paraphrase what has been pointed out elsewhere, take them out of their natural environment and a crime against nature is committed. It's like ponchos, Nepalese knitwear or dolphin steaklets.