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as I am in the healthcare field, I meet a lot of older gentlemen who wear shirts like these. I speak mainly of those wool shirts, usually with a plaid pattern, straight non button down collar and two chest pockets.

these older guys seem to know how to wear them. I am somehow beginning to like these shirts and see them often at the local thrift shops, but don't know how to wear it. What would you fellows wear it with without looking too fogey or western? What type of casual trousers or shoes would you pair it with?
 

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I loved these shirts while in college; still do. Especially old Pendletons or Woolrich models. For pants, works best with khakis or cords. For shoes, anything casual will do, except sneakers.

The legacy "trad" look from my era (Midwest, college in the 1960s) is to wear a solid color dress shirt, white or blue, underneath. Of course you have to be someplace that has reasonably cold winters.
 

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For trousers, wide-wale corduroys, flannel-lined khakis (or regular khakis with appropriately warm undergarments), wool flannel trousers in dark colors (chocolate brown, hunter green, etc.), or if the shirt has a slimmer fit, jeans or jeans-style finewale corduroys also work.

A long-sleeved undershirt (or a turtleneck, if you feel like mixing it up a bit) is a good idea, as the 100% wool shirts I've worn at least have been a tad on the rough side. A henley might also work.

For footwear, boots (Bean boots, Redwings, etc.) or mocassins would be my first impulse.

For outerwear, maybe a barn coat or field jacket.
 

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And for instructions on how to get the piss out of your boot, look on the heel (it works). Sorry, but it's not too hard to wear a Pendleton shirt. I always wear a t-shirt (any color) and usually leave the tails out. Jeans or whatever. It won't look "western" unless you really ham it up with some other accessories, also, IMHO, tucking it in is the first step to making yourself look "western." The western look, for me, begins when you try to make western-wear behave like dress clothes. Think Roy Rogers, or almost anyone from Los Angeles.
 

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I wear plaid wool shirt-jacs similar to this description nearly every other day. Put a t-shirt under them as they tend to be scratchy. Other than that, it's hard to mess up. I wear them with jeans, khakis and cords. I supose you could also wear wool pants if they have a suitably casual look (such as filson or bean hunting pants. I also often wear them with redwings or moccasins. The trick with wool plaid shirts is to keep them from looking to much like a specific stereotype. Boots jeans and a knit cap can make you look like a lumberjack. Cowboy boots and a hat will make you look western. Torn jeans and dirty sneakers will make you look like kurt Cobain. Try to avoid all of these.
 

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I agree youngster and spats about going for the casual look. Khakis and cords work fine. However, pair the shirt with some jeans and it might take it to the western side.

Good point here:
IMHO, tucking it in is the first step to making yourself look "western." The western look, for me, begins when you try to make western-wear behave like dress clothes. Think Roy Rogers, or almost anyone from Los Angeles.
I personally like a subtle western look. In fact, I just purchased this western shirt from Cacties and I'm really impressed with the quality and look. Again, that's just my style.
 

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This time of year, I change out of my work clothes and into a t-shirt & Pendleton combined with cords or khakis, pretty much every day. I don't much care if I look fogey or not, its just the warmest stuff I have. A couple of points:

1. Pendleton shirts are assembled in Mexico & China. New with Tag Made in USA shirts are regularly available on Ebay for about $30-40. Buy now. Supplies are limited. Supposedly NWOT are available in the hundreds and go for $10 ish.
2. Engineered Garments and Woolrich Woolen Mills have youth/fashion cut flannel shirts, also Made in USA. Pricey but guaranteed not to look like and old guy.
 
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