11/28/2009 05:12 am ET | Updated May 25, 2011

Midlife Crisis Shoes

Last month I took my son Blaise out to lunch at his favorite diner."Wait!" I implored as I teetered across the parking lot after him. "I can't go that fast. Walking in these new shoes is like walking on stilts."

Blaise turned and glanced down at my feet, encased in a pair of brand new embroidered espadrilles with 2-inch wedge heels. "What are those, your midlife crisis shoes?"

Definitely. With four kids in college and one in junior high, it's high time for my midlife crisis. Shoes are cheaper than a boob job, a tummy tuck, or a new car. That was my rationale, anyway, when I decided to spring for a pair of comfortable heels.

Except that now I had to wonder if "comfortable heels" was an oxymoron. Imported from Spain, those ankle-twisting espadrilles had called my name from the top shelf of a boutique while I was shopping with my daughter, Taylor. Taylor's blond curls, blue eyes, and perfect runner's body make her look runway ready in anything from flip flops to Gortex boots, but she's a sucker for pretty shoes. When she spotted these exotic espadrilles, she had to try them. "These are the most comfortable shoes I'll ever own," she declared.

Since I was footing the bill, Taylor urged me to buy a matching pair. "You'll love them," she said. I didn't. As it turned out, my luncheon foray in espadrilles was a near-death experience when I tipped over into a pothole, then had to curl my toes like Aladdin so I wouldn't fall out of my shoes while climbing up the diner stairs.

I came home feeling old. I grew up in the age of platforms, kind of like the ones Meryl Streep struts around in during Mama Mia, and I loved how they made me look leggy, hip-swishing, and, well, taller. I'm 5'3" on my best posture days, so wearing heels in my youth was a guarantee that I could reach the wine glasses on the top shelf. Besides my platforms, I owned red stilettos, pointy black boots, and working women's pumps. As a young woman I always chose beauty over comfort: I had lethal chandelier earrings that scraped my neck, tummy-tightening pantyhose and underwire bras that could come unleashed at any moment and stab me through the ribcage. God, I looked good.

Then, somewhere between motherhood and deciding to work in a home office, I took off my earrings and kicked off my heels in favor of sensible flats. My favorite shoes are black, round-toed Merrills that make me look like a nun, no matter how often I tell myself that they make me look like a British mystery novelist hiking the moors.

The night after my espadrilles escapade, I modeled the Merrills for my stepson Drew, who just finished a film internship in Los Angeles and is the family's resident fashionista. "What do you think of these shoes?" I asked.

"They scream 'unavailable','" he said at once. "But at least they're one step up from Crocs."

That did it. I set out on a mission. There had to be comfortable heels out there. After all, I am no reality show virgin. I've seen Dancing with the Stars. Those people don't just walk in heels, they dance in them! Even intellectual women manage to get around in heels. Sure, Supreme Court Justice Sonia Sotomayor fell and cracked her ankle while rushing to board an airplane in heels. But there she was, just minutes later, filmed using crutches but wearing a sexy black high heel on her good foot!

For my next foray into the upper reaches of footwear, I went with a pair of cute gray El Naturalista shoes stamped with abstract ivory designs. They had a respectable heel, just under two inches of comfy looking cork. I fell in love with the little frog label, too.

The woman in the shoe store gushed. "Naturalistas are made of all natural materials, so they're not just good for your feet. They're good for the environment!"

"Great," I said. "But can I walk in them?"

"You'll never need another pair of shoes," she vowed.

Okay, maybe she didn't mean to say that. What shoe clerk would ever tell you to put your wallet away? The point is, I bought that pair of shoes for philosophical reasons: I wanted to be a Naturalista! According to the company's web site, "Naturalistas start their journey observing everything that surrounds them. They travel through the world and observe it, becoming impregnated by its textures, its colors, its lines... and after a thousand journeys, real and imaginary, they discover that a single idea brings us together. Whatever our race or culture... we all walk in search of happiness. Movement is El Naturalista´s reason to exist. That is why we enjoy creating comfortable and attractive footwear, that helps us to move along the amazing journey of life."

Formerly impregnated with children, as a Naturalista I could now bravely move along in my amazing journey of life in environmentally correct high heels! I was ready to become impregnated anew with textures, colors, and lines.

Alas, my journey proved to be a short one. I wore my new Naturalistas to a marketing meeting - they went perfectly with my swishy gray mid-calf skirt and slinky black sweater - only to tear them off the minute I was out in the hallway an hour later.

"Cool shoes," my colleague Laura remarked as I was limping back to the car. "Are they comfortable?"

"Sure," I said through clenched teeth. "It's kind of like not noticing you sprained an ankle because your feet are on fire."

Maybe I was going about this all wrong. Maybe wearing high heels was like learning to ride a bike: I should start with training wheels before navigating stairs on a unicycle. On my next shoe store odyssey, I opted for black leather Ecco pumps with a 1.5" heel. These were more streamlined and less Croc-ish than my Merrills, more pilgrim than nun. Their motto was good, too, or at least shorter: My world, my style, my Ecco!

Alas, my world, or at least my foot, was too wide for an Ecco. After half a morning these shoes made my feet feel bound in baling twine.

"High heels that don't fit are a torture chamber all their own," I complained to my husband.

"Why are you even bothering?" he asked. "Men don't notice a woman's shoes. To me, women in heels look like hooved animals."

If my husband didn't care about high heels, why did I? I thought about the waitress who had served me in one of our local restaurants recently. She was French and wore high heels to serve scrambled eggs, along with dangling earrings and a beautiful bell-sleeved wrap dress. I wanted to look that put together at least sometimes.

Over the next few weeks I went through all of the shoe outlets north of us. I started with Ariats, Clarks, Danskos and other brands that advertised sensible comfort and offered chunky, clunky heels. The problem was that these shoes might be tall, but they were undeniably ugly. I might as well go back to Merrills. I moved on up to the pointiest, tallest dancer shoes, some of which had wraps and ties that made me feel like I should wear a toga with them.

At one point, I fell head-over-heels for a pair of gold Elites close to three inches high; these shoes had a gold patent leather upper and special cushioning inside that looked and felt like bath mats, with all of those little dots. I'd gotten smarter, however, and wasn't about to buy any of the shoes I tried on if they felt even a little bit uncomfortable. A shoe that's too snug or slips on your heel in the store will feel like a snake is biting your toes or a dog is chewing your heels when you wear it doing anything other than sitting down. I really wanted those Elites. I visited them three times, walking for fifteen minutes up and down the shoe store aisles during each of our encounters, willing them to be comfortable. Eventually, I had to give up. The straps around my heels weren't enough to keep me from sliding around. Even Cinderella, with her fairy godmother tailoring her shoes to keep her stepsisters out of them, couldn't have danced in those.

Finally, I went to the swankiest shoe store within an hour of my house and explained my situation to the patient clerk. What I needed, the clerk said, were heels made of top quality leather, because those would be softer. A pillow insole would be a good thing, too.

"Here," she said. "Try these." She handed me a white box with an abstract design in bright green and yellow green. Inside it snuggled a pair of black Joy Chen shoes with 2 ½-inch heels. The shoes had a closed back, an open toe, a wide elastic strap, and a snazzy gold interior. The heels were thick but not wedged. In fact, the shoes were shaped like an elegant bridge, or even a piece of art. I was instantly in love.

I tried them on. I walked around. My feet didn't seem to notice. I looked in the mirror and still saw a middle-aged woman in jeans, only this woman was elegant and lanky. I saw me, only better.

"Let's try one more thing," the clerk suggested. She ripped open a packet of little gray rubbery things shaped like clouds, called "Tip Toes," and thrust them into the Joy Chen shoes.

I put the shoes back on. "Wow," I said.

I walked. I jogged. I pranced in place. I had found my shoes! And the best part? They were on sale.

The next day, I had a meeting with an attorney over a house sale. I wore my Merrill's as far as the lawyer's parking lot, not wanting to chance driving in heels. Another obstacle presented itself as I got out of the car: a gravel path leading to a steep set of stairs made out of rough timbers. Could I do it? I cast a wistful glance at my abandoned Merrill's, but squared my shoulders and got out of the car in my heels.

There was nothing to it! I could have run up those stairs!

I shook hands with the lawyer, and I swear to you that he looked me in the eye, then did one of those looks men do when they think you're not noticing. It might not have been the shoes. After all, the shoes had inspired me to wear earrings and lipstick, too. But after the meeting, I drove home in my Joy Chen's with the windows down and the radio on, feeling like it was spring all over again.