I've never had a good Halloween costume. In middle school, Carissa was a pirate. Then I was a weak pirate for a few years, minus the patch, messed up teeth and grime. It was a store-bought costume made of cheap material and it didn't keep you warm at all. At the time, I admired the kids who could make their own creative costumes.
A few years ago, Jenny and I pseudo-dressed up and went trick or treating (well past the age where that was acceptable but no one can tell). We wore homemade masks and attempted to put together something that was slightly lame, as one woman answered the door and asked what I was. (By the way, I don't think this was a big deal or any of her business. I landed on her doorstep and she'd better shell out the candy. My half-hearted effort was still worth a few handfuls.) Like many holidays that our family celebrates, there isn't a whole lot of meaning behind it: On Halloween, it was all about how much good candy you could get; Thanksgiving was about how good the turkey/stuffing was; and Christmas about how good your presents were or how many you got.
Now, the costumes for teens and girls have become nothing more than a few pieces of cloth and baring as much skin as you can (princess, occupations of different sorts, Amazon woman...) As an "adult," I haven't had a chance to break out the creative juices, and it doesn't matter much. It will be nice to experience the holiday from a kid's perspective ... so for now, I must live vicariously through Ryan.