certain elements, i think, can be done well.
my father wore cowboy boots rather than engineer boots during the 50's, and that was southern tier NY.
Bogart wore a thin tooled ranger belt in The Big Sleep.
i wear a big vintage silver/turquoise buckle with a ringer tshirt and jeans.
but, if you mean boots/jeans/hat/etc. all at once i think you better have a local rodeo in your area to pull it off.