Sadly, I can't say I have ever dressed up for Halloween, however for my 21st birthday.. It was a dress up theme My mum, Dad, twin sister and I dressed up as the the guys from the wiggles..
Nothing I've actually gotten to do yet but on the rare chance I do get to go out- I'll be going as Marty McFly. I have the orange vest and everything.
I'm a huge New England Patriots fan, and the year that Tom Brady blew out his knee, I put on my Tom Brady jersey, Patriots hat, and a pair of basketball shorts, wrapped my knee in an Ace bandage, and borrowed a pair of crutches, and went as an injured Tom Brady. I then proceeded to get hammered and try to use crutches, which went about as well as you'd expect--I quickly gave up and started walking, which resulted in some hilarious double-takes.
I don't remember many halloweens growing up..but..one time in my twenties, I dressed up as a mime. I found out you're not very convincing as a mime if you TALK..lol
Nothing will ever beat when I took cardboard boxes, and made a Herbie costume. Yes, Herbie the Love Bug. I remember seeing my grandmother, who was at the time in great pain from all the smoking she'd done, waking up just barely enough to see me in the costume, and she grinned like the sun was new again. I'd never seen her smile like that. That is a moment I will never, ever forget.
None I can think of as a kid but this year is going to be pretty awesome. I was originally going to be a fairy but then I found a Harley Quinn shirt and hat online. I had wanted to wear it to work that day and then the fairy wings that night but unfortunately I found out from my boss that we are not allowed to dress up. Even if it's just a shirt and hat So I'm going to combine everything and be a Harley Quinn fairy for the night!