"I call this piece "eyebrowless wonder." I feel that the mottled gray background really evokes a sense of melancholy, even as the subject forces a metalmouth smile.
This was 5th grade, making it 1991, in Stamford, Connecticut. This was a private school with a dress code: for picture day we had to be in "formal" dress code, which consisted of a navy blazer or sweater, white shirt, and khaki skirt or slacks, thus creating a lifelong aversion to all of the aforementioned clothing items. I went to this school from 5th grade through high school, so you can imagine why I shudder at the sight of a navy cardigan.
Note the unfortunate-growth-looking hair tie, and strange crystal necklace. I had gotten my ears pierced over the summer and was very excited about my star earrings (visible on my left ear). I wore that same hairstyle/necklace/earring combination for pretty much all of 1991-1992.
I was not a well-liked child--I had one or two friends, but I think I was generally perceived as deeply nerdy, and a goody-goody as well since I got impeccable grades. My mom was the middle school art teacher, which didn't help (people liked my mom, but being a faculty brat was a strike against you, socially). I had a talent for drawing which was my one and only party trick; people would ask me to draw them a horse or a car or whatever and I could create something fairly convincing.
I am still deeply nerdy, but relatively well-adjusted, considering. I ditched the hair tie and discovered mascara the following year, and eventually my eyebrows darkened (a little).
I turned out to be one of Teh Gays. I have an amazing girlfriend, and people still ask me to draw them stuff." -- Lizzie