Once I was headed to a party where I didn’t know anyone. I made a paper mache mask of myself (with beard) and painted it accordingly. All night long people were perplexed. When I finally removed my mask I won the best costume award. Sweet!
I’ve always loved Halloween. Let’s see… last year I was a very close replica of Capt. Jack Sparrow (complete with Jagger walk and rum-smelling) Year before that, Anakin Skywalker complete with lightsaber. Year before that was a fullon pimp, I believe. Some good costumes I made as a kid were The Tin Woodsman and me and my two brothers made fullon wizards capes and staffs. We always had a plan of attack on the neighborhood too to get the maximum amount of candy. Planning was done a month in advace to see how we could improve from year to year.
Did you have the toilet seat??
ya gotta have the toilet seat
My best ever was as an ink-blot test. “No, really, what do you THINK I am…?”
It was a huge hit. 
He didn’t carry a toilet seat. Ordinary kitchen chair.
I once put together a Santa outfit and underneath I wore a flesh colored body stocking. All night long I “flashed” people.
Yes, I was the Flashing Santa Claus.
I like to do the classics but one year I ventured further out. I think a 6’2" Oompa Loompa can be very scary. The costume was pretty good but I could never get the green wig to style quite like an ice cream cone.
A friend of my daughter’s once went as a garbage can. The can came up to her shoulders, and she wore the lid as a hat. There was garbage up to her neck, and the overall effect was quite convincing.
The kicker, however, was her two pet rats circling the top of the can, around and around.
In 1986 I went to a Halloween party as my friend Martin Sykes, AKA "Beelzebub,’ author of the popular Blue Board C64 BBS software, and sysop of Blue Hell. (He was one of the hosts.)
It was a simple costume - trenchcoat, round specs, blond streak painted on, Super-8 camera. It was kinda funny because Martin was Very Tall and I was Not At All.
I guess it made an impression - that costume was mentioned in one of the eulogies at Martin’s memorial service last year, as an example of the sort of impression he made on us. 
During the height of the popularity of The Drew Carey Show, I (having a build very similar to that of Mr. Carey) got a crew cut, bought a pair of horn-rimmed glasses, and assembled a dull suit complete with a 50’s-era tie. Mrs. Homie, with the help of a seamstress friend and a copious amount of makeup, made herself up to look like Mimi Bobek (sp?).
We (Mrs. Homie and I) went to a local bar that was having a costume contest, whereupon we took second place and won $100.
Hmm…I guess my two favorites are Medusa, and a diet Coke can (two wire hangers straightened and bent in a circle, with white material draped over them, to make a cylinder, and red felt for the letters). I made my brown hair curly and sticking up on top of my head, like the soda coming out. Since I was known for drinking a lot of diet Coke, it was a fitting costume. I finally turned into one.
Your mom is a big ol’ party pooper. That’s awesome for a kid to think up.
Last year I went as Frau Blucher (whinny!) Had the gray bun wig, the dirndl-type vest and skirt, scarf, shawl, the mole - and the whinny, courtesy of a hand-held electronic recorder.
“Who are you supposed to be?”
“I am…Frau Blucher.” (Whinny!)
Was a big hit all night.
That would be the Tomorrow Knight mark 3.
Helmet made of sheet metal, I found in a garage. Beak, mylar stretched over the eyes.
Mirrored plates as a chest piece. Sheet metal epaulettes.
Metal and purple fabric bracers (fore arm armor).
Purple vambraces (shin armor).
Silver spear made from two old ski poles and a toy knife.
Huge mylar wings made from old tv antennae and thermal emergency camping blanket.
My best would have to be from the early 90’s. I wore black pants, a purple silk shirt unbuttoned to around my navel, and had died my hair dirty blonde, grown out mullet-length (just for this cotume) and blown dry to look featherd.
When people asked me who I was I started tap dancing in place with my arms hanging loosely by my sides.
Yes, I was Micheal Flatley, Lord Of The Dance.
- I was the Hermann Park Flasher.
I got a poncho, a pair of women’s pantyhose, some batteries, LEDs and a pressure switch. I hung one leg of the pantyhose out my fly after stuffing it and putting the LEDs in the end of the hose. When I raised up the bottom of the poncho, the giant tonker would come up with it and I would then press the switch and “flash” them.
Won first place at the party that year.
I’m a noob at picture sharing. This is my first attempt here.
I’m not sure about “best” Halloween costume, but here’s my highschool friends and me about, ohhhhh 34 years ago. I’m Paul.
Does the link work?
She’s not telling about the time she went as a belly dancer during a “White Halloween” we had when we lived in Durango, CO (elevation: 6512 ft above sea level). That was interesting…
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I was about six or eight years old and my father made me some kind of cardboard bird costume. when I pulled a string, the wings flapped.
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much much later, I went as a flasher wearing shorts and a military field jacket that came to mid thigh. on a hook in front of my crotch, I hung a bunch of bananas. They are gonna look at your crotch when you open the jacket. The trouble with that costume was that there were two guys in gorilla costumes at that party.
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Pumpkin lawn ornament. Cut out the bottom and stick it on your head. Done.
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When I was 8, T. Slothrop’s dad (who was also my dad) helped me make a paper mache bear mask, and put me in an ancient fur coat, so that I was a bear (with mothball accents!). I won a prize.
I would like to say that I wasn’t actually poking Jim in the eye with my light sabre, but I probably was. He should probably wear goggles around me.
Aw, shucks, t’weren’t nuthin’. 
I think my best costume was a Jeanie costume I made one year (Jeanie from “I Dream of Jeanie”); harem pants, little vest, slippers, and a pony tail on the top of my head - it looked really good.