Well, it's day 2. I don't feel like this is going to be much of a challenge for me, since I wear either : leggings with long shirts/short skirts or jeans + tee shirts.
Today I wore a black button up shirt underneath, a satin belt, some shiny leggings, a pair of doc martens that will not break in, and a cardigan. Good thing, too. It started snowing today when I was out and about. Brrrrr.
And now I'm in for the rest of the evening, so you'll excuse me while I go throw on PJs and watch terrible movies on Netflix.