Halloween costumes I have worn:
A princess. I always wanted to be a princess for Halloween when I was a kid. My mother made princess costumes for me and my sister when we were 5 and 7. Mine was pale green with an iridescent chiffon overlay and I loved it. I had a wand and a crown and little sparkly shoes and couldn't sleep the night before Halloween from the excitement of it all. Then my mother wouldn't let us leave the house to go trick or treating without coats (we lived in northern New Jersey at the time) so in the only photo I have of us in costume we're both wearing giant puffy parkas and look like we'd been crying. We had.
Columbia from the Rocky Horror Picture Show. I was in my early 20s and had planned on going to a party with a group of friends who were also supposed to be dressed like the Rocky Horror cast. They bailed, so I ended up at a different party where no-one knew who I was supposed to be. I still have the bustier and top hat.
A black cat. I was 19 or 20, waiting tables, and we were required to wear costumes, so I wore a black leotard, ears, and a tail. I figured I'd make more tips if I was a Slutty Kitty. I met one of my favorite boyfriends that night. He said he wouldn't have known I was in costume if it hadn't been for the black nose and whiskers I painted on my face. Meow.
A sexy housewife. I was taking my nieces trick or treating and decided to dress up in one of my mom's 1950s shorty nightgowns with marabou slippers. I didn't realize until we'd hit the second block of houses that the gown I was wearing was almost completely see-through, which explained why I later found three one dollar bills in my plastic pumpkin.
I have also been a Nun (and went to a party where there were three other nuns, one pregnant, all male), Joan Jett (complete with Bad Reputation and red Fender Stratocaster), Drunk Rocker Chick (technically, that wasn't a costume - I just walked around the block ringing doorbells with a pillow case in one hand and a bottle of Jack Daniels in the other), Dorothy Parker, and Marilyn Monroe with a nose ring (actually, it wasn't Halloween, but close enough).
Once I figured out I could play dress up whenever I wanted, Halloween lost some of its appeal. My nieces are almost all grown up, so I don't have an excuse to trick or treat. Plus, I don't eat candy anymore. Or drink. But the Irish Pagan in me still loves the holiday. Next year: Dublin for Oíche Shamhna.