Think about where you will be going and where you live. Are you going trick-or-treating in five degree weather? You probably should avoid wearing short skirts or sleeveless tops then. Is it 100 degrees where you live? Stay away from long pants and thick clothes unless you like heatstroke. cosplay
Decide where you will be wearing your costume. If you are going to a black cosplay costume contest get a cute costume. The majority of contest winners, unless very spectacular or in a specific category for "scary" costumes are cute/pretty/sexy/funny costume wearers. This means you should skip the Scream mask or the ugly wart-nosed witch, unless it's humorous. If you're just trick-or-treating, going to a party, or handing out candy, you can wear what you'd like within reason.

Think about who you will be with. Your kids, your boyfriend, who? Dress to suit, sexy not skimpy and don't forget be appropriate. The playboy bunny is not okay for a church party, but would be fine for an adult cosplay costume party.
Don't be someone no one will recognize. Even if you love Raquel Reed or Jeffree Star, the majority of people will not know who you are. If you hate the question "What are you supposed to be?", avoid unknowns.
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