Adam Glassman
Photo: Robert Trachtenberg
Q: I love cowboy boots, but when I see photos of Britney Spears in them, it scares me off.

A: Me too. Never, ever follow her example and wear them with miniskirts and bare legs; in fact, don't wear them at all, even with jeans or long Western skirts, unless you're vacationing at a dude ranch or auditioning for Oklahoma! Cowboy boots originally functioned to fend off sagebrush and rattlesnakes, but most ladies no longer need that kind of protection.

I was a cowboy boot addict in the '80s, so I know there's nothing more comfortable than a broken-in pair that molds to your feet. They're also fantastic as an art form. But unless you're trying for an urban cowgirl look, they're probably too costumey for real life. A hipper choice is the newly revived Frye boot. In a season of chunky, substantial footgear, it fits right in.