a hold-out yields to city bicycling in heels

When riding a bicycle in New York City first became a part of my daily routine last summer, sturdy leather shoes or boots worn with straight, ankle-hugging jeans or slacks became my all-season cycling wardrobe standards. Having come from years of road cycling, the idea of riding in a dress or skirt with high heels seemed exotic, at best.

What a difference a year makes. As my confidence in the bike lanes evolved, and I came to know many women who, true to the emancipating spirit of cycling’s Golden Age in the late 19th century, refuse to compromise their personal style or fashion sense while riding a bicycle, I’ve become increasingly curious about broadening my own sartorial horizons.

Until now, I’ve used public transportation to travel to meetings or events that call for dressing up. But especially in warm weather, I’d rather be experiencing all the pleasures of cycling.  So I wondered: How does one reconcile heat, wind, humidity and perspiration with looking fresh on arrival in a corporate or professional setting? Aren’t at least some concessions to bicycling apparel required to assure comfort and practicality?

I decided to give heels a chance. With the temperature registering a dry 65 degrees one recent morning, I resolved to pedal the roughly 30 minutes it would take to reach a meeting at which corporate attire would be required. Along the way, I discovered that just about every expectation I had about riding a bicycle in a skirt and heels was wrong.

All Dressed Up With Some Place to Go

Let’s talk about the clothes first. I chose the outfit shown in the photo above, consisting of a short-sleeved silk blouse, wool skirt, leather pumps and leather purse.

Because my city bicycle has a horizontal top tube, the skirt was a challenge. I picked one with a double back vent to help me haul my leg over the bar without ripping the seams. For modesty, I turned to the solution that every girl who’s ever hung upside down on a jungle gym knows intimately: pants under a skirt. In my only nod to cycling apparel, I pulled on lightweight tri-shorts. And I was glad I did, because the skirt hiked up not only when I mounted, but also (surprise!) with each pedal stroke.

The light padding in the shorts was a comfort bonus on the saddle since the skirt fabric was flimsier than that of most of my slacks. The shorts also disappeared beneath the skirt when I dismounted, so there was no need to change out of them at my destination. A new wardrobe standard is born: my tri-shorts will be getting a different kind of a workout this summer.

In the headgear department, I swapped my city cycling helmet for my racing model because its light weight and generous venting made “helmet hair” less of a concern. I wore my hair in a ponytail to keep the ends from losing their blow-dried shape in the wind.

How Heels Measured Up

While I typically follow routes that offer at least some bike lanes, on this day I had no choice but to ride through Midtown Manhattan — the area that the “Talk of the Town” column of The New Yorker once described, perfectly I think, as “anarchy without malice” for cyclists.

And here’s where those aforementioned expectations were confounded.

As I pedaled north on the west side of Third Avenue (to avoid the bus lanes), continuously on and off my pedals in the stew of traffic, idling delivery trucks and wayward pedestrians, riding in heels turned out to be — drum roll please — effortless!  In fact, I found that hooking my heels behind the pedals provided traction on push-off and added torque when pedaling.

While I would have thought that I would feel somehow more vulnerable in a skirt, it turned out that I had a sensation of being more “visible” to drivers. How? A few expressed their approval audibly (and, on this trip at least, politely), but most seemed to give me pretty wide berth, a phenomenon that’s been called “The Mary Poppins Affect,” and that I had also experienced while riding in snow during the winter. Thus, despite the complete lack of bike lanes on this route, I actually felt a little more secure on the road.

Similarly related to safety, I found myself riding more slowly than usual on my relatively fast aluminum frame — mainly in an effort to avoid sweating.

I also expected to feel encumbered by riding in more “formal” clothing. But I found that the sense of economy and efficiency that I appreciate every time I hop on a bike in New York City was heightened rather than diminished. I have no explanation for this; it’s something that I’ll explore on future rides.

No Time for the Ladies’ Room

In the end, the muted tempo of my pedaling also affected my travel time. Thus, I pulled up at my destination on East 61st Street 10 minutes late. I locked my bike up, clipped my helmet to my purse strap, combed out the ponytail, reapplied my lipstick and rode the elevator up to the board room, where the meeting was in progress. There wasn’t even time to stop in the ladies’ room.

As I slid into my seat with apologies for my late arrival, a colleague to my right whispered to me, “You road your bike in heels?”

“Of course,” I replied, “Lots of women do.” And I knew this was only the beginning of much bigger bicycling adventure.

Photo: Noah Wunsch


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