When is the best time to buy Halloween costumes. About 1 week after Halloween when they are 75% off. The boys enjoy dressing up so this was the perfect time to stock up on dress up items. I paid anywhere from $3 to $6 for the costumes and only ended up spending a little over $20 for 4 of them. I was able to find a captain, a swat team officer, an astronaut, and superman.
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