Not all gifts are regiftable: "Never regift handmade or one-of-a-kind items. Signed books and monogrammed items are off-limits. Some gifts that are good candidates for regifting include good (unopened!) bottles of wine, new household items and inexpensive jewelry."
Consider your intentions: "Don’t just give a gift to give a gift. Be sure that the recipient will appreciate the item. Remember, if you feel that an item is undesirable, the recipient probably will too." This is so true: a bad gift given once is enough. Put the bad giftgiving out of its misery and don't contribute to passing around an undesirable gift. The perfect scenario is if the gift is undesireable to you but perfect for someone else you know. A friend told us of receiving a western-themed decor item that wasn't exactly her style but perfect for another friend, who she regifted to with great reception!
Keep close tabs: "If you are going to regift, be sure you know who gave you the item, so you don’t return something to the original giver. Only regift items to people who are not likely to see the original giver." The same friend discovered she was once the recipient of a regift from her boyfriend (now husband). So, it looks like regifting-gone-wrong can have a happy ending, afterall!