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I don't have any Red Wing/Chippewa/Wolverine style work boots but wear SmartWool hiking socks for field work all the time and they're great. If I had a good pair of work boots they're what I'd most likely wear with them. Regular ragg wool socks from companies like Wigwam would also work pretty well, I would think.
I usually just wear thick black cotton socks, since they are cheap and comfortable. If you aren't going for fashionable socks, check your Army surplus store for some wool / cotton blend socks. They're usually a pretty good value. Personally, I find the smart wool socks a bit too thick for wearing all day. I have a pair, I wear them for hiking, but if I'm sitting at my desk all day, my feet just start to feel clammy.
I just go for cotton solid color crew socks for my Rust 1ks. Brown/Navy/Grey. I may get experimental with some non-solids but I haven't yet. Not a huge fan of thick wool socks but if it is cold they are nice. If your boots are like the 1ks they aren't lined at all so cold weather means thick socks.
Honestly, I'm a big fan of the classic, heavyweight hiking sock. They're definitely the most comfortable with any kind of boot, especially in winter. You can get them cheap from Costco this time of year.
I love these boots. I'm hoping to get them for Christmas. Just in case, I had placed an order with J Crew when they were showing a 1/19/13 ship date during the 30% off sale. (with a 60-day return policy, why chance it at that price?) Added a pair of clearance socks to push the order over $250. Unfortunately, my order was cancelled.
Honestly, I'm a big fan of the classic, heavyweight hiking sock. They're definitely the most comfortable with any kind of boot, especially in winter. You can get them cheap from Costco this time of year.
+1 on costco's hiking socks, 12 for 4 pairs if you're okay with a boring color. To me the kirkland brand felt less scratchy than the name brand one, which was 3 pair for 14.
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