I'm still a beginner and not very adventurous at all.
I know belting tops isn't a risk, but I was kind of nervous to belt sweaters because most people around me aren't doing that. I was afraid I'd look funny, but I liked the effect and now probably do it too much!
I bought leggings, which is so out of my comfort zone, and wore them yesterday under a denim skirt, but didn't really like the look even though a couple of my friends said I looked cute:
http://whenlifehandsyouapear.w.....today-ick/
I also got really layer happy this winter. I never used to layer anything but I saw on blogs that women are layering sweaters over sweaters, and pretty much any other combination out there, so I got 'daring' <snicker> and have layered woven button downs under knit tees:
http://whenlifehandsyouapear.w.....y-24-2010/
http://whenlifehandsyouapear.w.....ter-jeans/
It's not much, but for me, who basically lived in v-neck t-shirts and jeans before, it's been a stretch.