A first-day outfit that worked well: Last year I wore a multi-color sleeveless top from Anthropologie with white linen dress pants from New York and Company.
What I'll wear this year: This time I think I'll wear my sleeveless J. Crew purple shell with a black & white pencil skirt (the pencil says school, don't you think? :-).
Failed first-day outfits:
One year I wore a blue oxford shirt tucked into white pants. The shirt kept coming untucked all day--very awkward and distracting.
One year I wore a low-cut silky sleeveless ruffle-collared blouse with army-green pants (my pants said I meant business :). I kept trying to adjust my top not to show too much, and I don't think it was working. Later I turned the shirt around, clipped off the tag, and wore it with no problem.
Any stories you want to share about your first day outfits that worked or failed?
What are you wearing for the first day of school?
Good luck to all those heading back to school!