We CANNOT do cowboy boots. That is just wrong. I know the country music industry has been trying for years now to turn in usÂ all into some hicks by infiltrating the airwaves with country pop, but this is too far. Wearing cowboy boots does not make you funky and fashionable, it makes you stupid. Just because some artists are wearing it, does not mean normal people ever will, or will even look upon it well. Remember part of looking good is making sure that others think you look good. If they don't, and you're the only one that does, then you're just a fool.
If I hated cowboy boots, I think I would wear them just to tick you off. But, seriously, there are a few points to address here. First, not everyone who either listens to country music or is from south of the Mason Dixon line is a "hick." Granted, there's some pretty schlocky country pop crossing over into "mainstream" radio, but it doesn't suck any worse than the boy bands, teen divas, whiny frat boys and throaty Pearl Jam wannabes that make up most of the rest of that desolate audio landscape. Second, being "funky and fashionable" is only partly about wearing what other people would wear or would like to wear. In fact, if you limit yourself to what fits in that category, you're a mere slave to trends, and while you might be considered fashionable, you won't be very funky, and you'll never have style. Making others think you look good by simply catering to their expectations is no great accomplishment. Anyone can nick a look from a catalog, ad, or GQ spread and look decent. Now, making people think you look good when you put a twist on their expectations, or outright defy them: that's artful. And, when you do that, some people will probably think you look like crap. As long as you can still walk the walk (which takes some doing in underslung heels), the joke's on them, not on you. By the way, I don't believe there's any article of clothing you can wear that will actually make you stupid. However, if you're neither a country star nor an oil magnate, wearing cowboy boots with a suit would come close.