My office isn't that far from my house but there are bridges and a few steep climbs involved. I cycle in all sorts of weather. Winter, Spring, Summer, Fall. Snow, sleet, rain, freezing rain, ice, hail, high winds, you name it. I've only tapped out ONCE during my ride and took the subway home because conditions became so dangerous that I didn't want to risk it any further.

I ride in normal clothes. I ride in stilettos, high heels and sometimes flats. Whatever I'm wearing for the day. I've ridden in a Brooks Brothers custom suit with high heels to a meeting. Meh. I wear whatever I want to wear but I'm most comfortable in a pair of jeans and stilettos/high heels in the Fall/Winter and a sundress with flats or a low heel in the Spring/Summer.

You don't need to dress up like a spandex super hero to ride your bike. You also don't need to look like a fashion victim to do it either. Heck, you can even make socks and sandals hip. Trust me. Dress in whatever makes you happy and enjoy your commute!