In Toy Story, we see that Andy has a red hat, almost EXACTLY, oh wait, IT IS EXACT [white ribbon and all], to the one Emily, Jessie's old owner wore in the picture seen. But we DID see Emily throw out all of her cowgirl stuff. But Wait! The box wasn't very big, much less, big enough to hold the hat. Could it be that Andy's mom [AKA Emily], passed it down to him? What do you think? Let me know.
cred to @Emberwing for music