I wore a Betsy Ross costume, because I wanted one from the dime store (what we called the Five and Ten) for some reason. It included a plastic face mask. I remember nothing else about it except that I must have been carrying a flag.
I dated a girl I met at a Halloween party. She came dressed as a cockroach. She said she was protesting her landlord’s failure to do anything about them in her apartment.
Mine is a toss-up between a WWI German fighter pilot and a Stalinesque Red Army officer, both put together from items in my closet.
My cousin and I dressed up as snowmen to attend a Halloween party. We called ourselves Snow Clones and won a prize.
I bought a bunch of el cheapo baby dolls at the dollar store, then I dismembered them and stapled them to an old shirt. I was a pile of dead babies. I won a prize for “worst costume”.
I never dressed up in anything odd, but the funniest one I saw was a young troop in the military who showed up at a party with garbage taped/glued all over his clothing. Cigarette butts, candy wrappers, food scraps, you name it. When I asked him what he was supposed to be he said (drunkenly), “I’m just a fuckin’ mess.”
I’ve been so many weird things, it’s hard to pick just one. Among them:
- The set containing Chronos. I wore a pair of wire {curly braces} mounted around myself.
- The Northern Lights
- A Newton’s Cradle
- The constellation Orion
- A mummified firebreathing mutant vampire zombie alien robot dinosaur
- The vacuum energy
- A molecule. Ethanol, to be specific.
- A chesspiece. A knight, to be specific.
- A fire truck
- A bunch of grapes
- Great A’Tuin, from the Discworld books (the turtle that carries the world on its back)
- A 55-gallon can of Pepsi
I have a huge history of wearing odd Halloween costumes.
One of my favorites was dressing up as Hester Prynne from The Scarlet Letter. I was in the early high school years and thought it was a great and simple idea. Just past a red letter A on a long black dress. Hardly anyone knew who I was lol.
I’ve never had any grand ideas for a super obscure or weird costume but, one year around age 13, I settled on a fly mask with proboscis and compound eyes, a bowler hat, a plastic walking stick and wore a suit. Everyone asked me what on earth I was and I had no idea but it came together nicely and weirdly.
A few years back, it was Halloween and my daughter still had no costume ready. So I put her in a bomber jacket, track pants, Ugg boots, a 1930s-style woman’s turban, a white silk scarf, and my Ray-Ban aviator glasses.
Everybody knew she was supposed to be Amelia Earhart because the movie about her had just come out.
In San Francisco I used to run a huge halloween pub crawl. I put a lot of effort into my costumes, some of my favorites:
- Cthulhu for president (one of the election years, maybe 2012?). A full tentacled Cthulhu mask and a politician’s suit with a “why choose the lesser of two evils” button.
- Lionel from Dead Alive complete with lawnmower
- A Skeksis from Dark Crystal
Nowadays with kids grown up costumes are kinda an afterthought. Which TBH is kinda how it should be IMO, before coming to the states I thought grown ups doing Halloween was weird 
Back in 2001, I read about two people who took a pair of tall boxes, cut windows in them, covered them with flames, and had people jumping out. They put them on and went to a Halloween party as the Twin Towers.
A few years ago I was Frank Rossitano from the show 30 Rock. Most people didn’t know who I was supposed to be, and many others thought I was Wayne from Wayne’s World.
When I was in graduate school, and a member of a campus Christian group, we had a costume party at Halloween – though it wasn’t billed as a Halloween party, because it was a pretty conservative group. The theme was “come as your favorite Bible character.”
I wore a black shirt, black pants, black shoes, and black sunglasses. A number of people asked if I was dressed as the Devil, but I replied, “no…I’m the second character named in the Bible.”
Genesis 1:1-2 (emphasis mine): “In the beginning God created the heavens and the earth. Now the earth was formless and empty, darkness was over the surface of the deep, and the Spirit of God was hovering over the waters.”
These are awesome! I wish I had the energy to do something like this again!
Maybe spray your hair with deodorant and go as an armpit?
LOL! Now that sounds doable.
For a number of years I answered the door to trick-or-treaters dressed as Santa Claus! I did the laugh, and told them I’d be seeing them again in a couple of months. They were almost always flabbergasted.
I’ve always wanted to get dark glasses, sandals, and a volleyball and go as a nudist.
That would cause a bit of a ruckus I imagine. Plus it would be cold this time of year.
But an interesting costume.