If The Shoe Fits… - Las Peregrinas - Rebecca Liston

If The Shoe Fits…

By: Rebecca Liston

Dear Reader,

When I was in grade 8, I didn’t wear winter boots. Truth be told, I didn’t wear socks, either. Now that’s not such a big deal if I had been living in Florida, but no, I was deep in Southwestern Ontario, Canada, where temperatures dive way below zero and snow falls with a particular wet, miserable regularity.

I have a clear image in my memory bank of looking down at my feet, clad in what we called “Deck Shoes” (brown, cream tassels, the choice of anyone who identified as even remotely “preppy” at that time – it was the eighties, folks, we were an odd bunch) and thinking that I was pretty freakin’ cool. That I had somehow mastered the elements. That these shoes and I were Going Places, rain or shine or sleet or snow, even though they leaked brown dye all over my feet when they were wet, even though they had a rather dank smell by March, even though the sole came loose by May and flapped as I walked.

When trends change, as they do when you’re a teenager, and your older, much cooler brother is more aware of such things than you are because, well, he’s older and much cooler, and he insists that you trade in your Deck Shoes for a pair of Tretorn sneakers that he battles crowds to buy for you at Christmas because he knows they are All The Rage, well, you hang up your worn and torn beloved brownies and don the new, crisp, white sneakers and find yourself feeling quite chipper. You imagine a world in which you might play tennis. Or go to a garden party. And suddenly the posters of the brat pack on your bedroom walls seem…gauche. Immature. Silly, really. You decide to start reading the newspaper instead. And idly flip through The New Yorker. And you learn to drink coffee, one sugar, one cream.

And then…then things become more complicated as your high school years wear on, and you’re no longer certain you even understand what you’re reading and coffee, honestly, tastes gross and those Tretorns are tattered and grey. You ponder a return to the beloved Deck Shoe but note, with a touch of dismay, that no one wears them any longer and – gasp! – certainly no one wears them in place of winter boots! You try ballet flats. And some kind of loafer. And Nike sneakers. And then by some great gift of the Gods you find…Birks. And life as you know it is forever changed.

Birks. Birks with socks. Birks without. Birks with jeans and Birks with dresses. But never Birks on the dance floor – one just kicked them off and went barefoot at that point. Birks took me from high school firmly into university. Birks were Recognized. Birks were Understood. Birks were worn by Professors and Students alike. Birks were the great Uniter of Us All. Our calling cards. Our point of connection. Birks said, “I belong here.” And so, they went everywhere – from pub crawl to football games, weddings to Homecoming. 

But as all good things do, this, too, came to an end when I found myself faced with a Hospital Dress Code: “No open-toed shoes,” it read. (Can you imagine?!? The nerve!) And I, as a result, was catapulted squarely into my Work-Running-Shoe Era.

At least during the weekdays…and those pesky weekends I was on call…because at all other times I railed against the stiff, bulky weights of lead that were Work-Running-Shoes and tossed caution (and my ‘arches’) into the wind – Flip Flops, folks! Flip Flops were where it was Truly At! The squish of the soles as they became water-logged, the sound of banging them against the car after they filled with sand, the satisfying “flip flop” while I walked: Those things were not shoes! No, they were Freedom!! I was wearing Freedom on my feet!

And, in time, Flip Flops became Tevas (I grew less fond of the whole flopping around thing) and Tevas became Sneakers and Sneakers became, wouldn’t you know it, Running Shoes again (I said it was “for my arches”) until one day my teenager looked at my feet and proclaimed: “Mom, your feet look weird. It’s like they actually look old!” (Teenagers can be jerks.) And I realized with a shock that she was right (even if she was being a jerk).

Somehow, as I looked down at my feet, clod clumsily in my newest pair of Running Shoes, I realized I didn’t quite recognize myself. Whose feet were those? And more importantly: Where were they going? And even more importantly: What did they stand for? What did they mean? I wasn’t Running anywhere! Why in the world was I wearing Running Shoes, like, All The Time? Was it really “for my arches?” Had it just become some kind of Habit? Did I even like the darn things???

Three weeks later, I turned 50. My teenagers surprised me with a new pair of shoes. My teens, at the height of their Teenage Wisdom, with all their eyes turned squarely on The Trends, bought me a pair of powder blue Crocs. 


Yep, Crocs. 

Ugly, plastic-y, bejewelled-with-plastic-cow-faces-and-flowers-with-sunglasses Crocs. The very same shoes I would not have been caught dead in however-many-decades ago. 

Crocs: Just like theirs. 

My Crocs say, “My teenagers think I am cool enough to pull these off.”

My Crocs say, “I don’t care if you think I’m weird. I’m comfy and easy-going. I match everything.”

My Crocs say, “I might go into the garden and dig today. I might not. I might go get groceries. Or not. Heck, I might even go on a road trip in my big old truck. Or not. I might just sit here, on the porch, where it’s comfy and sunny instead.”

My Crocs are ready for anything. And everything. And all the things in between. And they’re weird. And brightly-coloured. And bejewelled and oddly-shaped. 

And that makes them pretty much perfect for me, for now.

Big love,


Rebecca Liston is cofounder and business intuitive at Las Peregrinas, a creative and consulting agency. She specializes in anchoring folks in a clear-eyed understanding of which path is theirs for the taking. She’s got one foot in the land of the subtle and unseen, and the other foot firmly planted in the land of ruthless pragmatism. Oh, and she swears like a sailor, which makes us love her more.

Get letters like this one, plus updates, insights, and invitations, delivered right to your inbox every week. Here’s the sign-up.

Want to read more?