First, I'm all about comfortable. The gum ball machine, with the giant clear trash bag filled with balloons is adorable...until you have to drive a car or use the rest room. Anything involving a leotard is usually strategically awkward, as well. However, I once wore a full length white slip over a black turtleneck and black leggings and I wrote "FREUD" all over it in magic marker. Ta da! A "Freudian slip" and still wearable under a dark dress! Of course good luck finding a slip these days. In this economy a "pink slip" works, too. That's pretty scary!
I used to own an opera cape which belonged to a Monsignor in the 1930's. It was a gorgeous (and warm) circle of black broadcloth, lined with satin and with brass crosses and a chain to keep it closed at the neck. I wore it to winter dances and over maxi-dresses in the 70's, but mostly it was for my witch at Halloween. It, in combination with my graduation robes from college (a present from a member of the class of 1924 and replete with moth holes) made a scary costume. I am very good at face painting. The neighborhood children lived in terror. But I gave it to a young priest a couple of years ago who wears it over his robes at funerals. The Monsignor has finally stopped spinning in his grave.
One year I wore a sheet stitched up the sides with a place for my head to poke out of the top and my arms to poke out the sides. On it was carefully painted a replica of a tube of Crest toothpaste, front and back. On my head was an inverted white paper paint bucket and I carried a car brush which looked like a toothbrush. Face paint did the rest. It was so comfortable that I couldn't understand why no one stopped for me when my car broke down on the side of the road. Hmmm.
I made my kids a Bionic Bunny costume with a sweatsuit, felt squares, a glue gun, a propeller hat, a bunny headband, and an Exacto knife. The cape came from the skirt of my favorite red dress, which no longer fit me after childbirth. That same cape, painstakingly hand sewn, has gone to college to be part of a Super PAC Man costume. My son is a political science major. I don't think anyone will get it, but he insists his friends are brilliant and it will be a big hit. Yuh.
But my favorite costume of all time is the Franciscan habit I borrowed from a friend. I wore an old man's mask with it, and pulled the hood over my head. I drank my beer through a straw all night. I pinned empty potato chip bags all over the front of the habit. That's right. I was a "chip monk".
Now for the really scary part of Halloween; living in the house with a bag of miniature peanut butter cups and Hershey's Kisses for a week!