What is your oldest toy (that you still have) from your childhood? My oldest toy is a Winnie the Poohbear plushie that is about 6 inches tall. I got him for my first Christmas (which means I was about 4 months old at the time), and I've kept him every since. He's going to be 24 years old this Christmas, and he is well worn and loved. I used to carry him around everywhere and snuggle him in bed until I was about 12 years old. I kept him on bookshelves until I turned 17 and moved to another state. He's been kept in storage ever since, but I still feel connected to him. He's a big part of my childhood.