As I got older, my costume ideas got more creative and I worked alongside my mom to make my costumes really good. My elementary school did some sort of costume parade every year, where kids from each classroom (there was only one classroom for each grade, my town was that small) lined up in grade order and marched around the playground so the kindergarten kids could be frightened by the scary masks the 5th grade boys wore. This one kid always came as a package of M&Ms. Even from an early age, I always considered the opportunity to dress up in a costume to be one that should not be squandered, and half the fun of dance recitals was the makeup and costumery. One year I hadn't seen the movie Return to Oz, but I'd wanted to, so I dressed up as a pumpkin head and got to wear orange makeup. In fifth grade I decided my costume would be "Over the Rainbow", and I wore a variety of brightly-colored and ranbow-striped clothing, a posterboard carapace with scenes I'd painted from the movie, a painted rainbow cardboard hat thing with birds on little wires above. That was probably my most creative costume.
Sixth grade I wouldn't settle for less than dressing as Mac Tonight (the moon-headed guy from the McDonald's commercials), and seventh grade I was a gypsy. I think eight grade was the last time I went trick-or-treating, because in high school I was either helping my friend hand out candy at her house (nobody came to ours, even our new house wasn't really in a neighborhood) or babysitting. I always had a costume to wear to school, though; my best probably being Scarlett O'Hara. One time I made this spider outfit with stuffed black tights and wire strapped on to make it look like I had four extra limbs.
The best costume I ever constructed was probably the year I made my own Sally from Nightmare Before Christmas outfit; I dyed my superlong hair red (it lasted a few days) and spent long hours finding the right fabrics and hand sewing everything. The last few years I've been so busy with this job in the fall (and two years ago we were in China) that I haven't done much in the way of costuming. Last year I put far more effort into Dan's costume than mine (I dyed my hair red again and did a Pippi Longstocking thing, while Dan went as Max from Where the Wild Things Are). This year I reused pieces from my wench bridesmaid's outfit and did a piratey sort of thing for a party we went to Saturday (Dan went as Indiana Jones), and changed the bodice and shoes and added jewelry and a scarf for a fortune-teller outfit today I'm wearing at work. It's a little odd to look down and see cleavage. There's a piece of ratty blue lace tied around my waist, just to add some authenticity, and looking at it I'm having all kinds of flashbacks about playing dress-up with the same piece of lace as a little kid. I don't know where it came from, but somehow I still have it. Maybe next year I'll use it as a veil and go as a Corpse Bride.
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Edit: two photos (one a coworker took, one I took myself long-armed)
Also today, I'm going to call my mom and tell her happy birthday. For some reason, holiday birthdays are common amongst my relatives, and my mom's birthday happens to fall on Halloween. It wasn't until I was around 9 or 10 that I realized we should be making mom a cake and celebrating her birthday in addition to planning elaborate costumes and eagerly awaiting a stash of candy to hoard until Christmas. In college I'd always make a point of coming home on or around Halloween (usually an associated weekend) so I could take my mom out to lunch or the movies or something. Lucky for her, she really likes Halloween as a holiday in itself and doesn't seem to mind birthday celebrations coinciding with costumes and candy. She dresses up every year it's on a weekday and her students usually sing happy birthday to the biker chick or the 50's teeny bopper or the witch. Being older and wiser now, sometimes I think back on my Halloween memories and wonder what it was like to have one's birthday completely overshadowed by something for one's kids.