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Biking in Heels: A Step-By-Step Guide for Stylish Ladies On Two Wheels

Photos by Molly DeCoudreaux, styling by Stone Pony

San Francisco is home to some of the sexiest sporty girls around. I’ve seen girls ollie over MUNI tracks in mini dresses, met women at cocktail parties who still have climbing chalk under their fingernails, and witnessed a parade of skirt-wearing ladies bike down Market Street. This week, I noticed something new - women biking in heels.

It makes sense in theory: you get to wear your favorite shoes to the club, don’t have to shiver in the cold waiting for a cab, and you can avoid the all-to painful wobbly walk to your destination. But to a sensible-shoe wearing dame like myself, the idea of riding in stilettos seemed unimaginable. “It’s not that hard,” said my femme friends. One even swore it’s easier than ordinary shoes. So I asked those stiletto-wearing, bike riding ladies to share their tips:



Choose the right shoe. You want stilettos, not platform. You need something to tuck behind the petal, or at least hang off the back. Choose ones with a grippy sole so you don’t slip. Thinner soled shoes work best so you can feel the pedal beneath your feet. For your inaugural heel ride, use ones with a back or strap, so you don’t fall out while finding your preferred riding style.



Ride on the balls of your feet. Anyone who rides in clipless pedals knows how to ride on the balls of their feet. In this picture, she is riding on Shimano pedals and swore it felt almost like riding in her bike shoes. Best yet, it really builds your calf muscles—just like walking in heels, but without the pain.



Tuck it! Some heel-riders swear by the tucking method; others say it felt like pedaling a paddleboat. This method works best if you have tougher heels and smoother pedals that won’t eat your shoes. These metal ones work great for tucking.



Own it! Biking is sexy. Heels are sexy. The two combined—fierce. So ride it like you mean it and while you’ll still likely get a lot of those “How do you do that?” questions (see above), you’ll also likely get plenty of props from the passersby.

Have any other tips for riding in heels? Share them below. And check out more of Molly DeCoudreaux’s Riding in Heels photos here.

Kristin Smith started riding bikes at 3-years-old and hasn't stopped since then. A long time rider, racer and commuter, Kristin has spent the last five years writing about San Francisco's active bike culture. She is the newly appointed Communications Director for the SF Bicycle Coalition.