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For me, it was while I was in middle school and I was a garbage lady or bag lady.. I am not sure what we decided to call em but my older sister had made me a costume out of some black garbage bags.I wore it to school . It was probably the worst costume I ever wore but I don’t think I thought that way at the time.
A year or two after my wedding I wore my wedding dress as part of a dead bride costume. It had already been dirtied a bit on the bottom from my outdoor wedding and was never dry cleaned and I didn’t plan on ever wearing it again anyway so i thought ‘hey why not?’ plus it only cost me like $75 from a thrift store when I bought it and wasn’t in perfect condition to start with. I think I looked pretty awesome , awesome enough that noone told me I shouldn’t be trick or treating because I was too old, instead i got compliments on my costume and extra candy from some folks
It was my best costume ever I think . My worst costume would probably have been in one of my teenage years where I was “too cool” to dress up or put in minimal effort.
My best was probably when with my friends as children, all three of us dressed as Jason and played a trick on this old lady. Instead of all going up to the door at once, we hid and went one by one.
As we did she became more confused each time and (and we might have even continued the rotation, can’t remember that part)… finally she said “Hey, haven’t you already gone through?” squinting her eyes in suspicion.
We laughed and ran away as children do.
I should start thinking about next Halloween’s costume for my daughter and myself. Maybe this will be our best year yet.
As of now, unless someone comes in here describing a costume too good not to try for myself, I am thinking of doing a Doctor Who themed set.I’d have to make it myself so i need to start early. Only have 294 days !Superman costume is good but with a pumpkin on the head….LOL!!! You can try your costume here
I dress up in a Superman costume but wear PinK underwear outside (to look different). It was the weirdest or embarrassing thing I ever did on Halloween. DC and Marvel character Halloween costumes were my favorite. From an early age, I used to buy those costumes online from my mother’s credit card without telling her.
It was my best costume ever I think . 
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