With my own children, there were more limits with Halloween. Most schools restricted dressing up to a costume parade held during or after lunch, so I had to make sure my boys could put their own costumes on since I was at work and couldn't help them. Masks weren't allowed at school or at the party for our church, so we rarely used those. We never went more than a few blocks when taking our kids trick or treating. It was more fun going to the houses of people we knew and they still got plenty of candy.
The most complicated costumes I made were the year my boys wanted Lord of the Rings costumes. One wanted to be Gandalf the White and I studied tons of photos so I could create the right kinds of layers of runics, robes, and capes for him to wear. The other son wanted to be an elf (not Legolas since no blonde hair) and I made a shirt, tunic, pants, belt, cape, and a bow. I also braided his long hair (both my sons had waist length hair like their dad) the same way the elves had theirs in the movie. A local costume shop had the pin to wear with an elven cape and we were set. It was awesome! Alas, never again!
Where we live (Utah), a lot of people bring their children by before it gets dark. That was hard for me to get used to when I first moved here. When Halloween falls on a Sunday, trick or treating happens on Saturday. I'm pretty sure that happens in places outside of Utah as well, but we didn't do it that way when I was a kid. My Halloween costume for this year is one I made last year, but didn't get to wear (long story - involves a car accident and a broken foot). I'm an IKEA bag lady. The corset and skirt are made from Ikea shopping bags. At 50 cents per bag, it was a cheap costume (even though it took a "few" bags to fit me). I put in some hair extensions to look different, too. The noise of walking in the plastic bag skirt eventually drove me crazy, but I was excited that I finally got to wear it.
The highlight for me this Halloween was my dear friend (who is the Chaplain at the treatment center we both work for) dressing up as a "Gangsta." The baggy clothes, sideways hat, fake gauges in her ears, long socks....so great! The hubcap hanging from the chain around her neck was everyone's favorite. Our Halloween tradition at work is to dress up in costume and have chili for lunch. Employees bring two cans of chili earlier in the week. One can is for the lunch and the other can is donated to the local food bank.