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If you have to ask if they're in or out, you probably shouldn't be wearing them. And yes, except in very unusual circumstances, they should be worn with jeans.
I think it depends on where you live. In the south, they are a regular part of one's wardrobe. Texans wear boots daily, with suits or with jeans and everythng in between, as do many in NM, Arkansas, etc. Here on the East Coast, it's a different story. Some guys can pull it off just fine. For some, it makes them even more rugged and outdoorsy (esp. if the boots are beat-up old leather (not exotic skins, of course), but for others it has the opposite effect. I've got two pairs that I wear about 3 times a year -- bought one pair (Tony Lama's) in about 1987, the other in 1990 (Lucchesse). I should wear them more....
I think the cowboy boot is decidedly out. That being said, that makes them the perfect piece to wear with confidence to show independence and style.
I'm a big fan of taking timeless pieces that are currently out of style and working them into your rotation. I think it shows depth of style and some flair. It's important to dress well and differently from the crowd. I mean, how many verticle striped multi-blue hued shirts can one bar hold?
I've worn them with jeans but was just thinking last week about getting a pair to wear with a suit. Actually, it'd be best to have one pair that could be worn in either situation. They're very comfortable.
I work at a large California University. This is the first week of classes, and I have seen 4 students wearing cowboy boots. They were the beat up, dirty kind, probably purchased pre-distressed at a premium. I've never seen them before this week. So, to that extent, they are in here.
In my neck of the woods--coastal California (I live in the southeastern corner of Los Angeles County and work in the heart of Orange County)--they are dead, dead, dead. I don't remember the last time I saw a man in cowboy boots. In fact, it's rare to see any man in casual attire wearing anything except the odious alternatives of sneakers and sandals, sneakers and sandals, sneakers and....arrrrgh....
I wore cowboy boots almost constantly for about 14 years or so until I began having foot problems. When I switched to shoes, the foot problems vanished, never to return. I think there's a lesson there. Today I consider them rather fatuous footwear UNLESS you are a real cowboy or some other kind of Western horseman or you live in Laramie or someplace similar.
We had a doozy of a thread about cowboy boots over on the Andy Forum. Turned into an ongoing political debate and raged on about all sorts of things.
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