My beret has been a successful foray into the had world. The beret, scarf, long sleeve top, trench coat and jeans have gotten me out the door faster on days when I didn't know what to wear. I look forward to finding a summer hat.
Other things I've tried that have pleasantly surprised me:
skinny jeans
skinny jeans tucked into boots
full length leggings under dresses/skirts
draped cardigans
batwing sweater
scarves
studded belts, bags and shoes
Angie's motgo of knee length denim jeans with high boots

I think I've gotten a lot of bravery from YLF and other fashion sites. My "risks" include:
very vintage looking pieces
browns (not just black)
booties (a total Angie influence!)
slouch boots
skinny jeans (I remember her first iffy post on them years ago)
colors!
scarves

Size 16 skinny jeans on my ample, pear-shaped body.