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.

View the discussion thread.

>I'm a skirt lover so I usually wear skirts every day and you're so right, its so damn sexy and I get men and women complimenting me all the time!

You know, I never hear men say "and I get so many compliments…!" WTF? Why is what strangers say sooo important? Why not celebrate the fun, feeling good, time savings, health and planet benefits, etc.?

Sexy is in the eye of the beholder. Some people pedaling in heels look sexy if they are, you know, sexy. Declaring oneself sexy is pathetic, grasping and renders one a not-credible witness. So embarrassing. Save it.

By Anonymous (not verified) on October 24, 2011

I ride in heels every day, darlings. I don't know that I have any advice, except Just Do It!

By Hillary (not verified) on September 27, 2011

I thought I'd send you a photo of "Eiko" who is in her 80's and rides every year in the New Jersey MS-150 ride where she rides the 150 mile, 2 day ride in pumps on her single-speed bike. In a skirt, of course.

http://www.flickr.com/photos/theskepticaloptimist/2896971648/

By Peter (not verified) on September 27, 2011

wow, how stupid is this blog....

By Anonymous (not verified) on September 23, 2011

Check out the MKS 3000 Rubber Block Pedals. They have a traditional look that especially goes well with classic-looking frames. Because they're all rubber, they provide perfect grip for dress shoes and other slick-soled shoes. You can order them online at Velo Orange.

By Cheryl (not verified) on September 23, 2011

Check out the MKS 3000 Rubber Block Pedals. They have a traditional look that escpecially goes well with classic-looking bikes. Because they're rubber, they provide perfect grip for dress shoes and other slick-soled shoes. You can order them online at Velo Orange.

By Cheryl (not verified) on September 23, 2011

I've been biking in heels for 10 years and I agree with Lily Ko. It's a cinch to bike in platforms and adjusting your bike seat high enough is key.

Also, if the soles of your shoes are slipping on your pedals, you can try putting on a couple pieces of duck tape for a bit more grip. You probably don't want to do this for your super nice shoes, though.

Under skirts, I wear "dignity protectors," smoothing undergarments that are like pantyhose that stop at mid-thigh.

By Melissa (not verified) on September 23, 2011

Wow, What a difficult issue to solve?
Oh wait, this is 7x7, not BBC.

By AJ (not verified) on September 23, 2011

I've been biking in heels for 10 years and I agree with Lily Ko. It's a cinch to bike in platforms and adjusting your bike seat high enough is key.

Under skirts, I wear "dignity protectors," smoothing undergarments that are like pantyhose that stop at mid-thigh.

By Melissa (not verified) on September 23, 2011

Great guide, I also recommend wearing a shoe that fits well in the heel so it doesn't fall off while starting up a steep hill (I've had this happen before, so embarrassing)!

Also, it's misleading to say heels build calves while walking. While heels are cute and all, they are so not for walking, and cause foot damage, back problems, and calf atrophy with long term wear.

By Anonymous (not verified) on September 23, 2011

I grew up in Europe and biking around the city in heels and skirts, or even in a suit, is an every day thing. Now in San Francisco I feel at home riding my bike to work every day and not having to worry about special shoes and clothing. Here are some of my everyday tips:

- First, learn how to ride a bike in traffic around the city.
You will look good and sexy only if you know what you are doing, you are respectful and share the road politely.
Don't hog the shared bike lane; think like a car so you can pre-empt traffic moves and avoid creating a traffic jam; stay on the right of your lane when you can; be mindful of other bikes and people that ride faster than you; keep an eye out for pedestrians that don't always look before crossing. And don't ever pass a bus on the right side. First get the biking part down, THEN wear more challenging and cute outfits.

- For maximum freedom and wardrobe options, make sure your bike has chain guard. If it does not, then you will need to roll up your pant or use one of those cute leather ties. This will prevent the fabric from being caught in the chain or from getting oil stains.

- Heels: I am all for them. I prefer to ride with the front of my foot on the pedal (like in the last picture of this article) so my heels won't ruin. This also avoids scratches on the part of the sole that is visible. It's true that the platform wedges work well too, and as the other reader suggested, you might want to adjust the saddle height with tall wedges.

- Pedals. Flat metal ones are the best. Try not to get those that are too spiky because they scratch the shoes and they slip more easily under your leather shoe sole... which does not make for a prompt and classy start after a red light.

- Skirts: wider mid-length skirts are the easiest ones. You can tuck them between you and your sear and between your legs, still leaving enough freedom to move. When I am wearing a shorter skirt, sometimes I tie a long scarf around my waist letting the ends fall between my legs. You can also let the scarf cover part of your legs if necessary. In general, if you are tucking your skirt right, there will be no risk of flashing anybody, but the scarf can give you that extra comfort when you need it and you can focus on the road. While I am writing this, I realize it sounds nuts, but it works. :-)

- Long skirts: my sister in Italy secures her long summer dresses with a hair clip. So when she's riding her bike to the market she does not have to worry about the extra fabric flying into the spokes.

- Be prepared for the workout. The street of San Francisco can be challenging, but your legs and glutes will thank you.

Riding a bike in heels is fun. Just make sure you keep yourself - AND those around you - safe, while also looking stunning!

By Gessica (not verified) on September 23, 2011

One of my biggest reservations about getting a bike was how it would affect my wardrobe. 6 months later and I can safely say the effect has been minimal! I wear heels all the time, ankle boots being my preferred option. I'm a skirt lover so I usually wear skirts every day and you're so right, its so damn sexy and I get men and women complimenting me all the time!

By T (not verified) on September 22, 2011

Love it! My one condition for bike commuting was that it wouldn't effect my wardrobe, so I've been biking in heels (and bike shorts under dresses) for awhile now, and completely love it. I definitely find it easy, although I don't agree with the no platforms -- I find wedges and platforms even easier since you still use your ball, but have a bit of heel support, too, due to the wedge! Granted, depending on the size of your platform, you'll definitely feel the length difference and may need to adjust your seat a tad!

By Lily Ko on September 22, 2011