Um, well, I LOVE Halloween, so I love stamping witches and then putting "Best witches for a Merry Christmas" and then colouring the witches' dresses in Christmas colours. I also have this dead-looking, twisted Halloween tree, and I like hanging little candy canes from it.
For more general ideas, I like using any critter stamp and sticking a Santa hat on it (easy enough to draw), or any critter with clothes - I just colour an item of clothing (like the shirt of pants) with diagonal red stripes like a candy cane...
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