I don't really notice a difference between nice underwear and cheap underwear. Then again, a three pack of CK underwear where I live is $35 for a 3-pack (in comparison to the wal-mart special that charges $20 for a 3-pack), and I classify nice underwear as $50 a pair. I think that silk underwear feels odd, and I have yet to find expensive boxer-briefs that are made from anything but silk.
Now when it comes to winter clothing, I invested somewhere up to $300 CDN for a set of Icebreaker base layer (top and bottom). The feeling of coziness wearing this base layer keeps me warm when the temperatures hit -40 degrees celsius, while being breathable enough to wear inside.
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