"FOOTLOOSE"

Jul 29, 2025

5 min read

Ruby slippers aren't the only shoes that can change a life.

Originally Post Date: 11.24.2020. Revised: 07.19.2025.

The principal shook her head. She didn’t have to say it out loud—and no amount of pious posturing behind her voluminous habit could hide it. It was obvious: “Immigrants… they just don’t get it.”

The issue at hand was my saddle shoes. She simply couldn’t understand how I managed to get the first—and in her opinion, easiest—requirement of an incoming freshman so wrong.

The acceptance letter to the Catholic all-girls high school I would attend had been explicit about the wardrobe: where to purchase the mandated gray box-pleated skirts, white blouses, and scarlet red blazers that distinguished us from any other school in the district. But when it came to shoes, we were left to our own devices.

My mother reread the letter carefully. With a tinge of embarrassment and that ever-present hum of shame that clung to her in this new country, she asked, “What is a saddle shoe?”

I shrugged. I didn’t know either.

We might have consulted our World Book Encyclopedia set, but that didn’t occur to us. And I’d never seen the phrase “saddle shoe” in Seventeen Magazine©. So, we turned to Mr. Kowalsky—the dour, middle-aged, how-the-hell-did-I-end-up-here shoe salesman at the local Buster Brown shoe store.

The Saturday before school started, my mother and I went in search of the elusive saddle shoe. Turns out, it wasn’t a brand—it was a style. And it came in two options: the traditional white with a black saddle, and a sleeker pair—jet black with a grayish/maroon saddle.

“Do you know which ones you need?” my mother asked.

I shook my head.

“Well... which do you want?”

I looked at the white pair. Boring. But the black? The black was something. I’d read somewhere that your shoes should always be darker than your outfit. Summoning my inner Vogue©, I pointed to the black ones.

“You sure?” she asked.

“Yes.”

Not convinced, but with no other evidence at hand, my mom bought the black shoes.

I lived so far from school that there were no school buses available in my neighborhood. So, on the first day of class, my dad drove me to school and dropped me off in the parking lot.

That’s when the humiliation began.

Girl after girl after girl descended from the yellow school bus, white saddle-shoed feet touching the pavement in unison. It was an endless parade and they multiplied like the menacing brooms in The Sorcerer’s Apprentice.

The only people on campus wearing black shoes were twenty-three nuns—and me.

“I didn’t even know they came in black,” the principal smiled, sarcasm coating her words. “But I know your poor parents must have paid a lot of money for these... ahem... interesting shoes, so you can continue to wear them for now. Be sure to carry this note at all times to avoid a detention for being out of uniform.”

Thus began my illustrious high school career.

Every teenage misstep, every moment of angst, I blamed on those shoes.

Didn’t get invited to the Christmas dance? The shoes.

Dropped a tray full of dissection leftovers in biology class? Shoes.

Didn’t understand why letters in math class would abandon the alphabet to join a numbers cult?Shoes, shoes, shoes!

When I graduated, I swore I’d never set foot—pun fully intended—in a pair of saddle shoes again.

And then I started taking swing dancing classes.

Both instructors wore saddle shoes. So did the best dancers in the class. And because I wanted to be one of the best Lindy Hoppers around, I broke down and bought a pair. At dances, we looked like the giddy, uncredited cast of Happy Days.

Little by little, I broke them in. Truth be told, they were comfortable. They were sturdy. And they protected my feet from partners who had enough trouble walking, let alone leading a dance partner.

I fell in love with swing dancing and I fell in love with those shoes.

Over time, the swing craze faded, and the swing dance community did, too, so the shoes took up permanent residence in my closet. Years passed, but I never got rid of them.

Then one day, I decided to wear them to work. As I crossed the parking lot, our HR Director spotted me. “Nice shoes!” she called.

She was the type who never missed a chance to offer a compliment, so I smiled and thought nothing more of it.

But once inside, a colleague walked past my office. He waved. I waved back. Seconds later, he returned. “Hey. You’re wearing saddle shoes.”

“Yep.”

“The first time I saw my (future) wife at a high school dance, she was wearing saddle shoes.”

“So… did you ask her to dance?”

We talked for eight minutes—more than we ever spoken before.

Later, in the breakroom, a coworker I’d greeted many times without a response, actually stopped to talk to me.

“You know, I have a pair of shoes like that.”

“You do?”

“Yeah… they’re golf shoes, though.”

That day I learned he was a scratch golfer, evaluated golf courses as a side gig, and occasionally wrote articles for a golf magazine.

Every time I wore those shoes, I learned something new about someone. From the boardroom to the factory floor, people connected to my shoes.

“My mom wore saddle shoes. I have a picture of her in them. She died when I was sixteen.”

“First time I kissed a boy, I was wearing saddle shoes.”

“I had to wear my sister’s hand-me-down saddle shoes to school.”

They weren’t just shoes. They were memories. They were conversations. They were connection. They were better than Dorothy’s red slippers because they didn’t need magic to transport anyone to another time. For an instant, they were already there.

I wore those shoes nearly every day - even to the nursing home when visiting my mom. One day, as I was balancing a laundry basket in one hand and a holiday wreath in the other, I heard a voice from down the hall:

“Hey! Ida’s daughter! Ida’s daughter!”

“Hi, Ms. Dorothy—do you need one of the aides?”

“No. I just wanted to tell you, when I was younger, I used to wear saddle shoes, too.”

I put the basket down. We were about to board the Memory Express.

Not everyone felt the same way about my shoes. One resident, a gentleman who often sat in the activity area, offered this: “My wife wore shoes like that in high school. She was a bitch then. Stayed that way till the day she died.”

No one ever said the scenery in the rear view mirror had to be pretty.

But the person who loved my shoes the most was a senior staff member at the nursing home. One day she called to give me a progress report on my mom’s health.

“Before we hang up,” she said, “Can I tell you something unrelated to your mom’s status?”

“Absolutely.”

“Guess what Santa—that would be my husband—is getting me for Christmas?”

“No idea.”

“Saddle shoes! Ever since I saw yours, I’ve wanted a pair. So, I gave him all the ordering info. That’s going to be my Christmas gift. I’m so excited! When this is over, we should both wear them and model them together!”

I promised we would. We wished each other a happy and safe holiday and hung up.

Funny, the things that bring people together….who could imagine it would be a pair of shoes?

Is there a childhood item you once resented, only to fall in love with later? Tell me your “saddle shoes” story.