I like to have my students extend this short story by writing about what happens next in the story. Some like to write about ways in which the couple can enjoy their seemingly useless gifts, others write about how they can get the watch and hair back (interesting I know). What do you think happens to the couple after Christmas?
O. Henry intentionally made his tale sad but not tragic. Jim could get along perfectly well without his gold watch, and Della found that she really didn't want such a burdensome head of hair again. It seemed as if she had been spending half her time washing and brushing and combing all that hair and then putting it up in an enormous Gibson Girl bun on top of her head. Both of them faced up to the fact that they were poor and that they had been motivated by vanity, Jim in showing off his gold watch, Della in displaying her long golden hair. By giving up these material possessions they arrived at greater maturity. Both realized that their greatest riches were in their love for each other.
I'll play the optimist as well. I think Jim and Della's gift-giving habits were forever changed by this Christmas. They probably always found unique and personal ways to bless each other and demonstrate their love, knowing that gift-giving should always be about love and it's even sweeter if there's sacrifice involved.
I am afraid I have a more optimistic view of the next chapter of this story than #3, as much as I appreciate engtchr5's flair for the dramatic. I think the end of this story makes it clear that what is important about Della and Jim is their love for each other, based on their willingness to sacrifice what is important for them. Therefore the combs and the watch chain become symbols of this sacrificial love that sustain Della and Jim through the hard times ahead, through having children and raising them, and then finally bequeathing them to their children so symbolically they can learn the same lesson.
Due to the severe depression that befell the country shortly after this story, the family eventually fell into complete bankruptcy, and they had to sell both the combs and the watch chain to afford food.
When their money finally and completely runs out, Jim takes a job as a door-to-door salesman, telling Della that "He's not too proud to beg." The plan falls through, however, and the family winds up in the bread line before everyone dies of hunger-induced illnesses. Because no one really knew the Dillingham-Youngs, no one showed up to their funerals, and they were buried without any legacy to speak of. Happy little tale, ain't it?
Della kept the combs, of course, and her hair eventually grew out long enough to be able to wear them. Much later, on their oldest daughter's wedding day, Della gave the combs to Mary for the "something old" in the traditional wedding rhyme. These combs were handed down from daughter to daughter, and each time the story was told of the love Jim had for Della and the sacrifices they made for each other.
Jim eventually found a much better job and was able to buy back his grandfather's watch. He did not become proud with it, though, as Della had imagined he would, pulling it out more often to check the time and show it off. Rather, he wore the chain and watch with fierce pride and admiration for his wife, and he never looked at the watch again without remembering his dear, sweet wife with her newly shorn hair. He, too, passed his watch and chain down to their son, Joseph, who treasured it as his father had - not as an example of material wealth, but as a symbol of the love his parents shared for the 63 years they were married.