How to Bicycle in Heels

People are always asking me, “How do you bicycle in heels?” I must state for the record that more men ask me this question than women. But my female friends have asked me, “Do you carry flats in your bag?” My response is always, “It’s easier to bicycle in heels than it is to walk.”

Walking with the bicycle to cross the street. This is NSW after all.  J.Crew green suede heels. Leona Edmiston dress.

When the television show, “Sex and the City” was current I used to marvel at the distances that Carrie could walk and even run in heels. I reminded myself that that it was Television. In reality, when I lived in Manhattan, I could only manage to walk a city block or two before crippling pain set in. You know, the kind that makes you feel nauseated with every step that you take? You find yourself turning and weakly lifting your hand for a taxi. A whispered and hopeful, “Taxi, please” in the face of oncoming traffic. Or perhaps nowadays in Manhattan it’s, “Uber. Uber. Where is my phone?”

My favourite J.Crew green suede heels and Tahari dress.

I rarely have this problem now. I walk a short distance to my bicycle in the garage. I ride to the office/lunch/dinner/meeting/event. I find a post or a bicycle rack near the front door of the venue. I lock the bicycle and then walk a short distance to my destination. Afterwards, I ride to my next destination and repeat the above process.

The how of bicycling in heels is quite simple. Pedalling with the heel of one’s foot is like swimming without kicking, i.e. Not very efficient (and a little bit stupid). Place the ball of the foot on the pedal for optimal leverage. It makes starting easier and climbing hills less difficult.

The type of heel that I choose to ride in is based upon my outfit and the season. I have a favourite pair of Geox t-strap black patent heels. I like the t-strap because the heels stay on securely. I have a pair of green suede heels from J.Crew. They stay on my feet because I place the ball of my foot on the pedal to keep them on. A pair of Chanel heels that I bought second-hand in Minneapolis. “Old-lady” heels from Easy Spirit that resemble Chanel. My wingtip Aerosoles with three-inch heels that I wore in Seoul years ago which made me a giant amongst Koreans. And in winter, tall boots with various heel heights keep me warm and stylish.

I bought these Easy Spirit heels after the birth of my first child as I wasn’t used to wearing heels anymore. Quite comfortable for walking but even better on bicycle. Leona Edmiston dress.

Heels that I avoid on the bicycle? Mules or completely backless heels. I have never lost a heel on the bicycle but a clutch once came loose from my back rack straps on Pitt and King Street. A driver saw it fall off and sounded his horn a moment after I heard it land. He waited patiently for me to retrieve it. I smiled and waved at his kindness. Retrieving a lost heel might be a similar process but less obvious and definitely more embarrassing.

Aerosole wingtip heels in cordovan and pink with three inch heels are pretty comfortable but again better on the bicycle than for walking. Lululemon rainjacket. No tights during this slightly wet autumn day. Easier to dry off legs than to deal with wet tights.

Finally, the “how” of cycling in heels is not to different to cycling in general. I always “set my pedals” before starting. All of my shoes have a worn spot on the right toe area because I always set my pedal as soon as I stop. As I am right-footed, I place my pedal in the highest position, 11 o’clock, with my right foot. When it’s time to alight, the big push down with my right foot makes it easy for my left foot to come off the ground. Immediately, I position the left ball of the foot on the pedal.

This video doesn’t exist

To stop, I grip both brakes to slow the bicycle. I have my seat height set very high to gain maximum leverage from both legs. This seat height is a more advanced setting often used for road cycling or mountain biking and clip-in shoes. Consequently, I stop by simultaneously gripping both brakes and putting one foot and another foot down – one and two. I find that I lead with the balls of my feet again, not the heel.

This video doesn’t exist

If you have a lower seat, it’s even easier to stop. Use your brakes, lift your foot off the pedal and put your foot down on the bitumen.

Classic stopped position. Pedals set for takeoff. J.Crew heeled short boots.

Make sense? Confidence is key here. If you lack confidence, try with a kitten heel or heeled sandal and work your way up to greater dizzying heel heights.

No problems with balance on the Nihola tricycle but a little more walking today with kids and a short heel on Bruno Magli sandals.

Go out there and try. It will make the world a more beautiful place.

Happy Bicycling!

X Sarah


  1. ‘All of my shoes have a worn spot on the right toe area because I always set my pedal as soon as I stop.’

    Ha – ‘you know you’re a cyclist when…’, eh? 🙂


  2. Hi Sarah,
    I think pedal type makes a difference too. I have trouble with my heels slipping when riding my hybrid (which has metal sharks-teeth type pedals), but no issues with my electric bike with flat pedals.


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