When I moved to Boston, I noticed that ladies seem to wear ballet flats at all times. There would be snow on the ground and I’d see someone in ballet flats. It would be below freezing and some girl would be walking around with no stockings and her bare toes shoved in a ballet flat.

I thought I was on top of things because I moved from a Chaco-and-Keen wearing college town and purchased a practical and professional looking ankle boot, but no. I was wrong. I needed tiny ballet flats. However, I’m no tough New Englander, and I couldn’t wear them until recently, due to my toes turning blue when travelling sans-wool-socks.

I’ve come to realize that I probably wasn’t meant to wear delicate looking ballet flats, because they make me look incompetent on my bicycle. I’ll continue to wear these forever, but I have to remember to limit myself to Mary Janes for future purchases. I use a large pannier attached to a standard size rear-rack on a touring-ish bicycle made for short people. I wear a standard size shoe, but my feet are above the 50% size for my height. I’ve brushed my ankle on my panniers multiple times before, but never understood the potential negative consequences because my usual shoes (Merrell or Keen urban types) are sturdy and fairly unattractive. My delicate little ballet flats are not up to the challenge.

In terms of transferrable lessons: if your bicycle is more panther than kitten, and you use obscenely large panniers, your delicate-stretchy-cloth slip-on-style shoe will come off your foot and fly into traffic at least once a week. This will only occurs at high stakes intersections, in rush-hour traffic, and other situations where you are more concerned with matters of life-and-not-life, rather than the millimeter-scale positioning of your foot.  so you have to be ready to ride barefoot. The solution would be to: ride a bike with longer chainstays, find a narrow pannier, get an extra long rear rack, or stop wearing pretty shoes that are impractical for your lifestyle. I may consider getting a longer rack at some point in the future when I feel wealthier than I currently do. I already find my chainstays to be plenty long (440 mm!), and have no desire for a more relaxed frame.

Is it so wrong that i continue to wear them despite their impracticality? no, I don't think so.

I was super happy to come across these spectacular silver flats on clearance at Sudo Shoes, but their practicality extends to the fact that they’ve been run over multiple times and still look great. That will be my new test for all of my new clothing items:  ”how well do they survive when a bread truck rolls over them in the middle of Mass Ave?”