Cruel Shoes by
(24 Stories)

Prompted By Shoes

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There isn’t room for one more pair of shoes in my closet. But fortunately I haven’t been out shopping for shoes for a while. You could say it’s thanks to the pandemic. But really? It’s because my feet hurt. And my back hurts. I look at all those beautiful shoes sitting there–the perfect navy blue pumps, my all-time favorite shoes to look at, but the most painful of all; the sexy Italian taupe leather toeless shoes with wooden heels; the fuck-me black high-heeled boots–and realize that every pair has a story. And every story has its shoes.

When I worked as a nurse after college, I wore white nurse shoes. Unattractive but comfortable, probably in part because my feet belonged to a 20 year old, not to a 73 year old woman. I could stand on my feet in them for 8 hours at a time and feel no pain. They were ugly. Not at all sexy. But they were part of the uniform. And I wore them with pride. I wouldn’t mind having a pair of those on my feet right about now.

When I worked as a journalist I wore comfortable flats that worked well with my tweedy reporter look. Brown, boring, but comfortable.

When I had a boyfriend in New York where we trolled the streets at night, I wore the black boots until I couldn’t stand it anymore. I took them off, walked in my stockinged feet back to our hotel and he carried my boots.

When I took my first job in the corporate world, my boss gave me some instructions. “Get your hair cut (I had a big Jew-fro at the time), shave your legs (can you believe it?), learn to put makeup on, and go buy a navy blue wool suit, a white blouse and a red scarf. And get some high heels.”

I kicked and screamed and objected, but he promised me if I did all that and learned his script, I’d make enough money working for him to put my daughter through college. So I decided to try it for six months and see if it really worked. To this day I recall the pain of wearing that dark wool suit and high heels with stockings, in the hot sun, going from door to door, talking to small business owners, so I could pay for my daughter’s education. The pain was worth it. I worked for him for a couple of years and learned everything he had to teach me about looking and acting professional. My daughter went to college and I continued to wear different versions of that same ‘uniform’ for 30 years in my next career as a financial advisor.

Over those many years, I have to admit, I learned to love shopping. I loved dressing up in well-made, beautiful suits and handsome, if painful, shoes. Often I’d come home and realize I’d left my shoes under my desk at work! (My office was across the hall from my home.) But they looked great. ‘No pain, no gain,’ right? Or is it what my high school boyfriend had taught me, ‘You have to sacrifice comfort for beauty.’ In either case, I kept buying shoes. Different shoes looked great with different suits.  Even though they were all black or navy blue. I didn’t need a sales person to convince me. Hems rose and fell over the years. Heels rose and rose. Until one day I realized I was crying in pain.

New Balance became my new best friend. I wore them everywhere except when I was seeing a client. During that time I gritted my teeth, focused on our work together, and felt no pain. But when the appointment ended, the shoes came off. At the end of the day, the suit came off. The shoes came off. The bra came off. The sweats came on, along with the New Balance. It was a huge relief.

And as time went on, as I worked less and less, as I neared retirement, I found myself more and more recapturing my original look. I let my hair grow, I stopped shaving my legs, I stopped wearing makeup, and my many navy blue wool suits and their associated shoes languished in my closet. Now they sit there, abandoned, forlorn, still beautiful, some barely worn, and I don’t have the heart to throw them out or give them away, though I know I’ll never wear them again. Well, maybe, once in a (navy blue) moon.

Profile photo of Penny K Penny Righthand

Characterizations: been there, funny, well written


  1. Brava Penny for your life story told in shoes!
    Time now to relax and put up your feet!

  2. Oh, I LOVE this story! I wore those nurse’s shoes when I owned a little deli in Hawaiii and worked 12 hours a day;, a pair of fuck-me high-heeled boots when I lived in Vegas, except mine were a gorgeous purple suede; pumps in every color but mine were comfortable. Of course I didn’t do all the walking you did. No longer barking, your dogs must be wagging their tails now.

    Beautifully told…thank you, Penny!

  3. Suzy says:

    Great story, Penny! I can totally relate. Well, except for the nurse’s shoes, I never had those. When I was practicing law, I had the painful shoes that looked great, but I wore sneakers going to and from the office and carried the shoes in a tote bag. And if I wasn’t seeing clients, I would walk around the carpeted office in my stocking feet. Sometimes I even left my shoes under my desk at work on purpose! It’s probably time for you to give away those suits and shoes to someone who will wear them.

  4. Marian says:

    This is so relatable, Penny. I wore similar clothing (and shoes) toward the beginning of my career, but luckily things changed because of being in a creative profession and then in the Silicon Valley. I am relieved that you are now going for comfort!

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