I doubt that my friends would consider me particularly fashion-conscious, and I do work at a pretty relaxed place. Still, I do hit on on a good look or two once in a while, and have bought some nicer dressier things recently. I wear a lot of thin wool longsleeved tops that are incredibly versatile. The nicest ones, usually with a zipper that gives a deep v-neckline look good with knee-length skirts, dressy pants, jeans - and I can wear them home cycling afterwards
Crew necks look really frumpy on me so I'll add a scarf on those.
I also wear a lot of knitted dresses, some of them wool. The best look on me is sleeveless, since I have big shoulders that tend to pull at a closely fitted dress. My favourite is black and mid-thigh with a loose cowl neck, and looks relaxed with coloured woolly tights and flat shoes, or elegant with sheer tights and low heels. It also looks really cool with my 60's style knee boots.
I'm not going to win any trend prizes, but it's nice to feel I can choose to look stylish enough when I need to.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett