The first one is from Team Fortress 2: Chieftain's Challenge. Not only it is a headdress worn as an cosmetic item, but it is a commodity to be traded and sold (in TF2, hats are rare cosmetic items that can be traded for). I find this caricature of a Native chief deeply offensive.
Comment: Thanks for writing, Wilbur. I think you nailed the problems with these items.
For more on the subject, see Video Games Featuring Indians.