Well, first thing I did when I unjaydubbed was to give away ALL my sensible modest skirts. For five years I wore only jeans, bright comfortable tops, and flat shoes. I looked so unjaydub that a friend of mine, when he first saw me, thought: "I like her a lot, but I think she's a lesbian..." Biggest compliment I've ever had!
Then, not sure why, I started femming up. Now I wear lonnnng skirts, preferably with side slits, and broomstick "hippie" skirts for folk dance. Also pants, but they're either sedately rich-looking or gaudy now. And I wear high heels, but sturdy ones. And lots and lots of jewelry, minimum of three rings, and earrings, and gaudy hair clips to keep my waist-length brunette-and-silver hair out of the way. I'm even graying gaudily: most of it is in one streak over my right temple, and it's silver. I look good in black, but I also favor (and look good in) gray and purple. I have some pink garments that look good with all this trust-fund hippie stuff. I love garments with interesting textures. One of my favorite special-occasion tops is snug and black with specks of rainbow-refraction glitter all over it.
When I get home from work I put on a nightgown, but one of my nightgowns is a short tunic of snake-patterned silk.
Still don't wear makeup though -- I hate the way your face sweats off when you think too hard.
I think Tatiana has a good point about color matching. But for the most part, my clothes go together because I say so.
GentlyFeral
"There were cockroaches of course,
but very clean cockroaches."
-- Julia Vinograd