Ah, I love sweater vests. I've loved them since I was a high schooler and one of my favorite teachers wore them daily. Even at 16 (holy cow--that was more than half my lifetime ago!), the combination of nerdiness, irony, and practicality appealed to me--although I didn't start wearing them myself until I came out as a lesbian and decided I could wear whatever I wanted.
Breaking *some* social rules somehow frees me to break others. When I'm not dressing how a woman is "supposed" to dress anyway, what do I care if people think a sweater vest is dorky, or calculator watches have come and gone (again), or that blondes shouldn't wear mauve lipstick?
Just kidding about the lipstick(!), but you get my point: being seen as per se "deviant" already means there's more room to break rules, add some random pieces to your wardrobe, and have fun with what you wear. Worry about what looks fashionable and hot and attractive on you.
What are some of the miscellaneous fun fashion items you've got in your closet this fall?