As I mentioned on the Christmas Tree page, our tree growing up featured a lot of red glass bulbs and then a mish-mash of keepsake ornaments. I inherited most of those "keepsakes" (i.e. Homemade in Kindergarten) and they now hang proudly on my tree every year. There are many that I admire and smile at as I hang them- the felt ornaments, now completely falling apart, the pinecones with googly eyes glued on to make them look like owls, the silly toys that have doubled as ornaments for years.
But my personal favorites (patting myself on the back here, but oh well) are the pair of Debbie’s Brains. They are so ugly and so stupid, but I made these in grade school and I love them. Each one is a melted piece of circular plastic with broken glass inside. There is a curly ribbon tied through them so that they can hang on the tree. They are so ugly.
And I love them the best. Even more than the ornaments my own kids have made. Shhhhhh.
Another item I have that I consider a family heirloom and, in fact, it sits on my desk year-round is the first Christmas decoration that my parents bought together. It’s amazingly tacky and I amazingly love it.