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Don't wear them, 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 (fryeboots.com). In a season of chunky substantial footgear, it fits right in.
Above: Frye Boots ($248) are today's cool version of cowboy boots. They've been around since 1863, but I think they still look modern because they're simpler, more rugged, and a lot more comfortable (no pointy toes).