You have obviously never worn Lucchese (pronounced "Loo-casey") boots.
I have some of your preferred riding boots but find them less than fashionable in the foothills out here and not nearly as comfortable.
Cowboy boots are all about context. Don't wear them to the office, don't wear them to bars, do wear them outside with appropriately weathered, appropriately snug jeans and a loosely buttoned western shirt. Sans hat, unless you want to look like a dude. Except if you are a professional cowboy, which I am not.
And never, ever tuck your jeans in them. That just screams "dork".