Heel, girl

A sore thing
Until I walked three days in a $345 pair of red-hot four-inch Chie Miharas (House of Sole, 1237 S Michigan Ave, 312-834-0909; pictured, right), I never thought of wearing high heels as an emotional experience. But when I find myself sidestepping down my stairs, I realize the magnitude of this challenge.

The first day is pure fun—I channel my inner Carrie Bradshaw  and flash a knowing smile at construction workers on my way to the El. My snaillike pace gives me myriad opportunities to check my silhouette in storefront windows, and I like what I see: a flaunted bust, a tucked-in tummy, and long and lean stems.

Passersby notice, too: Women stop me to fawn over my footwear; waiters rush to my service; and the kind male employee at Whole Foods tosses a compliment before fetching some ripe bananas.

But as much as I enjoy the attention and the novelty of looking so va-va-voom, my emotional state spirals into exhaustion. I wrestle with acute pain in the balls of my feet and severe self-pity. Several buses scoot away inches in front of me; there’s no way I could run to catch them. Walking anywhere takes almost twice as long. And by the time I remove my shackles at the end of each day, I’m left with battle wounds: calluses on the soles of my feet and pinky-toe blisters, which result in a temporary hobble.

When the assignment comes to an end, I slip giddily back into my tattered Vans. I still want to take these saucy kicks out for nights on the town, but only with plenty of cab fare in my back pocket, so I don’t have to watch another bus leave me behind.—Jessica Herman

Which of our writers is the best at navigating the city in high heels? We put them through a series of tasks from navigating subway grates to running for the train. Click the video below to see who doesn't just talk the talk, but also walks the walk.