Originally Posted by commutebybikech

I typically wear a cardigan, tailored shift dress with compact ballet flats and just strap my pumps to the top of the rack. I switch them out when I get wear I'm going. I have definitely cycled in wedges before when going to BBQs and the like. In winter, I add a couple layers of leggings, two gloves, balaclava, boots and a jacket that has a bit of flex but works for the office. Its Chicago, its SO cold. In summer, I wear non-visible bike shorts when riding my track bike. On my dutch-style, its less necessary. I've got it down to a system that works for me. Its interesting to see different strategies.

I've got one CEO who rides in from Hyde Park to Skokie ~25 miles a couple times a week as a training ride. He's full spandex and showers once he arrives. It all depends on your lifestyle but I must say Chicago is a great cycling city. I say that despite being hit by cars twice. Hopefully Rahm keeps it that way. I hear Active Transportation Alliance is on his transition team.