As we welcome October, the return of The Walking Dead on AMC, and the celebration of all things layered and Pendleton when it comes to fall clothes, it's time to mention the Great American West. Specifically, whether men can really pull off cowboy gear — the hats, the boots, the yoked shirts — in any respectable manner worthy of style in 2011. So we turned to two men who live in the same city, but have very different views, for this week's Blogger Showdown. James Fox, of the excellent 10Engines, is in full support, while Giuseppe Timore — of An Affordable Wardrobe and host of the Boston area's great Top Shelf Flea — is staunchly opposed. Cowboys (or not), discuss.

James Fox: Cowboy or "western" shirts have been part of my uniform since the invention of eBay. It was all the fault of those Sears & Roebuck catalogs from the 1970s. Remember those?

Giuseppe Timore: Before someone outs me, I'll put my cards right on the table. There was, in fact, a time when Western shirts were a part of my own uniform. In my younger days, I played drums in a Rockabilly band. I wore my hair in a high, greasy Pompadour with sideburns down to my chin. I favored high cuffed jeans, and when I wasn't wearing a silly punk t-shirt, you can be sure I was wearing a cowboy shirt. Then a funny thing happened: We took a tour that landed us in Georgia. We stopped some place to gas up and eat. I got out, decked in my cowboy shirt, and headed for the diner. A surly fella in a cowboy shirt with a beer gut nearly as big as his belt buckle immediately said to me "You boys ain't from around here, are ya?" "Nope, Boston." I replied. "Huh," he snarled, "figures." In that moment, I began to feel silly in my western wear.

JF: You think the belt buckles are too big? No way. Can a steak be too big? I bet you have had a cote de boeuf pour deux by yourself, right? OK, dinner-plate-sized belt buckles are hard to pair with Weejuns, true. That is why God invented woolen pants.

GT: You see, I come from the antithesis of the places where these clothes are worn, the Northeastern United States. I work in a wine shop, my backyard is concrete, and the only cows I ever see are on a plate next to a glass of Bordeaux. Besides, my feet are too wide to fit into those narrow, pointy-toed boots, and cowboy shirts are more than a pinch goofy with penny loafers, too.

JF: But those shirt snaps are just so damn practical. Your cuff wont snag on machinery (or a corkscrew) but rather pop apart. To replace a broken snap, you have spiked interlocking pieces and a form that you have to hit with a hammer. That's how a man should be replacing his buttons.

GT: While there is plenty of truth to what you say, I must remind you that so much of the appropriateness of these things is situational. For example, even though we reside in the same town, I know you often head for the woods on the weekend, frequently find yourself in a barn, and are always attending the slaughter and roasting outdoors of entire animals. So, for you, this kind of thing may be deemed entirely appropriate. Things are a little different for "college boys" — a term frequently used derisively by the true Western-wear set, by the way — who buy their "cowboy" shirts in the mall at American Eagle. And while a man may repair his clothing with hammers and such, a gentleman has a tailor.

JF: It it a massive missed opportunity on the part of the consumer if he's buying mall-cowboy attire. Why buy a $29.95 MSRP bogus stand-in when you can have the real deal Clark Gable'd Rockmount for the same price (sawtooth pockets were devised to allow easy access to your drawstring tobacco pouch, don't you know).

GT: In some sense, isn't anything disingenuous if worn only to follow a trend?

JF: Wearing anything well is partly situational but being aware of the history of the cowboy archetype is recommended here: "Fictional cowboys are never bored. Real cowboys were often so bored that they memorized the labels on tin cans and then played games to see how well they could recite them." — from a fantastic article called "Ten-Gallon Hero" by David B. Davis.

GT: Style is about so much more than doing whatever happens to be "of the moment." This is why some guys can do this sort of thing and others can't. Clearly, a cowboy can wear a western shirt with Wranglers and a giant buckle. No one will think twice. But imagine that same dude wrangling ornery cattle in khakis and a shetland sweater. Ridiculous. Besides looking silly, the clothing has nothing to do with the activities being performed while wearing it. We've been seeing this for years with all the lumberjack outfits in Manhattan office buildings.

JF: I still say the western shirt (as the thin end of the wedge) has transcended style "moments" as opposed to perhaps the lumberjack "look" or sailor's toque. Sure, some fashion experts will push the western influence look every few years, just as they pronounce "the year of the white shirt" often, but since we (ahem) don't follow fashion or trends, that should not bother us right?

GT: Don't get me wrong, this isn't to say that no city-dweller should ever wear such a thing. A guy with style can do what he likes. The cool young professor at the university, maybe he can wear a cowboy shirt with a tweed jacket. A real rugged dude can wear one, because it will be honest, and it won't be his shirt that tells you he's rugged. Even a skinny kid in a rock band, maybe. But when this kind of rule-bending becomes too lenient, it turns into mindless conformity.

JF: As you touch on above, some of it is about confidence in what you are wearing, and for some, that can come from educating oneself about sartorial history. Personally, I love the image of an old cowhand stirring up the coal and coffee in the morning wearing a battered Shetland sweater. Maybe under his denim jacket, sure, but when the weather is shitty, there is no such thing as bad taste.

GT: Let's put it this way: Wearing this clothing doesn't necessarily have anything to do with riding horses, chopping wood, roping cattle, or eating beans out of a tin can in the dessert. But if the very idea of a given guy doing any of these things is downright laughable, then that guy should be careful with this stuff. Clothing is supposed to make you look good, and looking like a poseur never looks good. That being said, there are worse things than looking like Robert Redford in the '70s — so long as you're handsome.

Who won this showdown? Let us know your thoughts about urban cowboys in the (new) comments section below...

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