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Oct 12, · The 17 Weirdest Halloween Costumes Of No other night promotes weirdness like Oct. 31, so there can be a lot of pressure finding the most outrageous outfits and kooky costumes to wear. We’ve made it easy for you. Our guide features the strangest stuff to wear this Halloween, all in various stages of tastelessness. May 25, · Halloween is an exciting holiday for many in American culture. For kids, the holiday is a highlight of the year due to trick or treating, which is when kids go door to door to collect candy from their neighbors in honor of the day.