Over at Naked Villainy, the Air Marshal raises the question of re-gifting: giving as a gift something that you yourself received as a gift. He's against it, as summed up in his closing statement, "Re-gifting, to me, says 'You aren't worth my time or effort, so here you go.'"
I would argue that the appropriateness depends on the gift, the occasion, the original giver, and the new recipient. If you receive something that you just don’t like, and give it just to get rid of it, yes, that’s thoughtless. But how less thoughtless is the person who just buys gifts because they are obligated to without putting thought into what they purchase? On the other hand, some of the nicest gifts I've ever received were "used", but that word doesn't do them justice. They were items that belonged to friends, things they had received or purchased for themselves, which they enjoyed and valued, but the item reminded them of me and they knew I would value it even more highly. The item was unique or expensive enough that they could not purchase a duplicate, so they sacrificed their own for my happiness (my friends David and Brian are especially notorious for this). This seems more like a statement of "You are worth more to me than this item, so there you go."
I suppose part of my perspective comes from growing up relatively poor. We never had enough money to buy all the nicest things everyone wanted, but we put a lot of thought and effort into choosing just the right gift within our budget. Even as an adult, this rings true. The nicest gift I have received for Christmas from The Feared Redhead was also probably the least expensive, and was not new: She found a copy of BH Liddel Hart's History of the Second World War in a used bookstore for me.
Or take as an example the Air Marshal's own admission of passing on bottles of wine. If he won't drink them, and someone else will like them, why not pass them on? It's a simple gift given when attending dinner, it's not like you're one of the Magi carrying recycled Myrrh to Baby Jesu. Of course you should make sure you don't present a bottle given to you by your host or one of their other guests, but beyond that, I don't see the harm.
Ultimately, if you completely reject re-gifting, you're saying that what matters about a gift is how it was acquired. And that means that what really matters is not the giving of gifts, but the buying of them. And I reject that materialistic standard. I don't care how much of your money you spent on my gift. What I want to know is, how much love did you invest in it? The giver of the first Christmas gift invested His all, but not a single dime of money. Can't we invest a bit of ourselves without breaking the bank?