by Wendy
Follow me on twitter @wendylooksleaps

Jack and I met up after errands on a mild Spring evening and decided to walk to a popular French restaurant in a trendy neighborhood. We were seated at one of the cafe tables lining the sidewalk in a row. The weather was perfect for outdoor dining, and we ordered wine and steak frites. As I strolled back to our table after a quick trip to the powder room, I spotted it. A beautiful shoe. Kind of a platform, ankle strap, with a high, colorfully-striped blocked heel. Like a shoe out of those mesmerizing Dolce&Gabbana magazine ads where everyone’s wearing elegant black lace or vibrant sundresses and giant sparkly accessories while chowing down on pasta in Sicily – and it all looks impractical and totally believable at the same time. I didn’t notice the shoe owner’s outfit. She had her leg crossed and the cool shoe was dangling out there daring all of us to be jealous. I nearly stopped to compliment the shoe and in a different mood, I might have. Instead I returned to Jack and our lovely evening, a bit more conscious of my choice of ballet flats.

I thought about those shoes the next day. I used to be the girl wearing the cool heels. Sometimes, I still am. In my 20s, I wore eye-catching shoes all the time. Now there is a kind of mathematical formula I follow, like:

Estimated distance I have to walk

times probability of blisters

divided by the beauty of the shoe

to the power of whatever confidence I get from wearing heels for that occasion

= Whether I opt for cute flats

Heel-arious, right? I’m serious. Consider these crazy shoes I bought during my first trip to France in the 90s and wore constantly when I returned home – to class, shopping and errands, part-time jobs, dates:

How did I pull that off? Please try to picture these battered shoes when they were gorgeous. They haven’t been anywhere in 10 years because they’re faded and falling apart. The leather was peeling off on my carpet when I took the photo.

Now consider the heels I wore to work a couple of days last week:

Nothing wrong with these, and one of the most versatile styles. But they won’t cause any double-takes in a restaurant aisle. And I had spare ballet flats in a desk drawer in case I needed to venture farther than the Starbucks around the corner.

Maybe I’m out of practice.

The thing is, I really love my flat metallic sandals and riding boots and ballet flats and Converse. That night we went to the French restaurant, I had been traipsing around the city all afternoon. When I met up with Jack, we walked another five blocks or so, enjoying the weather and each others’ company. I know Jack is happier when I can amble for miles without complaining about my feet (or gasp, stumbling) than when I wear really cool shoes. This is critical when we’re traveling and there are many new streets to wander.

I don’t miss wearing heels all the time, but also don’t want to lose the skill. After revisiting some of the neglected pairs in my closet, I think I’ll make an effort to work heels into the rotation a little more often. I wore taupe wedges with jeans to a recent Sunday afternoon party instead of my go-to ballet flats. They were pretty comfortable so I didn’t object to running some errands afterwards…especially since we were driving.