My mom wore my favorite costume to a Girl Scouts Halloween party.
She wore black pants, boots, gloves and turtleneck, painted her face red and wore a cheap red tinsel wig. She was a burning match!
Well, we’ve been to a few costume parties, but the costumes that got the biggest and best response, were when we dressed up as big yellow chickens. We went down to the local costume rental place and picked these costumes out. Nobody recognized us. We showed toting large buckets of KFC chicken tenders. Yes, we were big chickens who ate our young.
Our friend went with us dressed as a wizard. As the night went on, and we had more and more jello shots and good beer, my hubby and wizard friend exchanged hats. So, the wizard became…The Chicken Gizard Wizard. Probably, doesn’t seem too funny to you, dear readers, however, when we’d imbibed quite a bit, it seemed funny at the time.
I once took my mom’s thick blue-robe, put curlers in my hair, then painted my face white, around my eyes with black (dead woman), drew snake punctures with blood all over my face, took a long toy snake and wrapped it around my neck.
My and my friends got trapped for 10 minutes in front of a house belonging to a little ‘off’ lady, who kept talking about the pet boa snake she had.
It was a damn cold night too!
Last night at my Halloween party a guy showed up in a cowboy hat, boots and a silver snake thong. That is all he wore.
A trio showed up as the three stooges. I also had a tourist, the crow, satanic priest, vampira dominatrix, a ghost and assorted witches.
There were too many priests at the party last night… too many to count.
This year at work I showed up as a painter who had fallen off of his scaffold.
I did the full-on George Romero blue zombie-style makeup, with the rotting flesh and everything, wearing the absolute most nasty old torn up painters outfit, with an old paint bucket and brush hanging from my waist.
I knitted a chicken hat one year. My idea was that it was the sort of hat a priestess of the Chicken Goddess might wear. There were two chicks peeking out from under the wings.
I wore it to work on Halloween, and my buddy Patrick saw me with what looked like a chicken on my head, and, free-associating, said, “Look! Merrily got laid!”
Then he realized what he said, and turned beet-red. It brought down the house.
I told the story at knitting guild, and it stopped the meeting right in its tracks.
In sixth grade, my mom made me a Headless Horseman costume. The top where the head was cut off was made to look extremely bloody and gruesome.
I won first prize. 
My daughter (age 2) was the most beautiful witch and won 1st place in the costume contest for her age group for the second year in a row. She is now 2 for 2 in Halloween costume contests.
EEEYAAAGH! Cannibal chickens!!! Now that would’ve scared the crap outta my ex. She was afraid of chickens! (Like a phobia or something.)
I think the costume I’m most proud of was my evil pinata. I got the idea from Squee, which has a story of a little girl eating candy on the evening of her birthday being visited by three angry pinatas chanting “You were laughing when you did it.” I made a mask out of paper mache, bought a dark red pijama suit, and spent a lot of time covering them both with paper. Polished it off by carrying a cardboard tube with me to beat people with. The most effort I’ve put into a costume since I was a kid, and it went over rather well, I must say.
I guess “my best” because it was so effective, but also my worst idea. I’d just moved to Arizona for graduate school. I didn’t know many people at that point. I decided to go as a KISS groupie. (I’m a dude.) Went to 2nd hand store and got some slutty looking shorts, sunglasses, ‘ho’ shoes, and foam “falsies”. Bought some hosiery and had my (female) neighbor fix my somewhat long hair and do a super-deluxe make-up job. The make-over took all day. For good measure, cut off pencil erasures and glued one strategically located on each falsey and wore a tight fitting KISS T-shirt for effect.
Went to the Department party - no one recognized me right away, so I revealed my identity (to raucus laughter). One of the female grad students showed up late with her macho boyfriend. Before long, while she was in another room, this guy starts paying attention to me and my “nipples”. This part was really surreal - I seriously couldn’t tell if he knew I was a dude and was just being friendly or was busting a move on what he thought was a hot piece. But then he cools it when girlfriend returns (whoa! Now I know.). She found out my identity and laughed big and told her boyfriend. All of a sudden, he’s obviously embarrassed and turns fighting mad and comes toward me, cussing and threatening to kick my arse. I took the advice to RUN out of the house and leave while others restrained him. Stayed home the rest of the night.
That was over 20 years ago and was the last Goddam time I ever dressed up like a female for Halloween.