How Low Can I Go? A Breakup Story  

I remember the exact moment I decided to kick my heels to the curb.  

I had worn 4.5-inch booties to meet a girlfriend for drinks. We were in the middle of a chat about our holiday plans when my friend interrupted me, pointed to my feet as if she saw an alien and said,  “OMG, you are wearing heels!”

In my mind, I wore heels all the time. The reality was a few inches lower than that. Her obvious shock at my footwear selection that evening made it abundantly clear that I had become, “The girl that wears comfortable footwear.”   

Ending an abusive relationship with my shoes didn’t happen overnight. Like so many painful relationships, I was so deep into it, I didn’t realize how bad it had gotten. 

For years, I loved nothing more than to put on a pair of high-heel sandals. I felt thinner, sexier and more feminine. For my job, I was required to dress up often and heels were a part of my uniform.  But there were signs that this romance was slowly ending. 

First, there was that night out, dancing to celebrate a friend’s birthday. For everyone else anyway. I lasted less than a song and then my date and I sat on the sidelines for the rest of the evening as my feet ached with pain. I didn’t touch those shoes again until I packed them off for consignment. Buh bye!

Then, I started packing a supply of band aids in a melange of shapes and sizes for different blisters every time I left my house in heels.

Soon, my beloved heels, which in the past were worn daily, were demoted to “taxi cab dinner” shoes. I would only wear them if most of the evening was spent sitting. Any unexpected situation that required me to stand for more than, say, 60 seconds seemed like an eternity. One never realizes how many restaurants and bars have concrete floors until they are on the outs with their stilettos. 

The final nail in the coffin in my relationship was when I struck out on my own career-wise and no longer had a corporate card to fund all my car rides. I got a Fitbit and embraced walking everywhere, but I still had to look good for appointments and events. I needed a pair of shoes I could wear for long periods of time without intense pain.

And then it happened. I fell in love. This time with a pair of Phillip Lim black leather “Alexa” booties with a sister-wife approved 1.5-inch stacked heel. With that boot, I could look fashionable without the balls of my feet throbbing or my toes pinching. I happily walked for hours without having to stop at every Starbucks I passed for a rest. That was four years ago and I haven’t bought a pair of high heels since. Once you go flat, you never go back.   

That last sentence isn’t completely true. Breakups are hard. If I do get together with one of my heels, it’s for a quickie, a one-night stand, a “booty call” if you will, and I regret it the next morning, if not much sooner. 

These days, I have loafers, 2-inch ankle boots, clogs and six pairs of Birkenstocks in regular rotation. If I am having a weak moment and missing my heels, I pull a pair out of the depths of my closet. Nothing too high, or that forces my toes to cram onto each other like New Yorkers on a subway. These days, I am not too proud to bring a pair of tennis shoes or flip-flops in my bag to change into.

I’m sure you’re all dying to know if it’s possible to have that “High Heel” feeling in flats? Sure it is. It’s all about feeling confident in your stride, no matter how high or low to the ground you are. Squishing my wide feet into tight shoes, and trying to walk with cracked heels and toes was so excruciating that I can’t imagine I looked particularly sexy anyway. 

These days, I’m walking tall, heeled or not.