That Day I Said Goodbye to Heels (And Hello to My Sneaker Collection)

4 min read

There wasn’t a violin swell or a dramatic slow fade, but I do remember the exact moment it happened: the day I looked at my stilettos, sighed, and quietly admitted, “We’re through.”

Like many women over 50, I’ve always had a complicated love affair with high heels. On one hand, they’ve felt like instruments of torture, bad for the arches, impossible for catching a bus, and frankly a little medieval in their design. On the other hand, nothing quite rivaled the instant boost, both in inches and in attitude, that came from slipping into a sharp pair of Prada kitten heels.

Wasn’t it Coco Chanel herself who quipped, “Keep your heels, head and standards high”? For years, I believed her. I used to gaze at the rows of designer stilettos in my closet, half in awe, half in disbelief, wondering why I ever thought I needed so many.

Should I sell them? Keep them as relics of my “heel years”? Even after Covid, when the world embraced practical footwear, the message lingered: heels were outdated, masochistic, and more costume than clothing.

Actually, letting go has felt less like a loss, more like liberation.

It wasn’t betrayal, it was evolution. After all, my heels and I had been together for decades. We’d strutted into boardrooms, wobbled out of weddings, and suffered silently through cobblestones that were clearly designed by medieval heel-haters.

Heels gave me an extra three inches of confidence and the illusion of calves sculpted by Greek gods. But the truth? They also gave me bunions that now deserve their own zip code.

Enter the sneaker. Once the preserve of gym rats and teenagers (do you remember the Flashdance style?), sneakers have tiptoed (comfortably) into fashion’s inner circle. These days, they’re not just acceptable, they’re aspirational for many midlife women.

Pair them with a floaty midi skirt and you’re suddenly “French editor chic.” Slip them under cropped tailored trousers and you’re “CEO who meditates before breakfast.” Even with a cocktail dress? “Très modern”.

Wear Sneakers, But Make Them Elegant

Gone are the days when sneakers meant clunky trainers destined only for aerobics class. Today, sneakers are polished, versatile, and perfect for women over 50 seeking casual chic footwear ideas.

Think buttery leather in soft neutrals, subtle metallic trims that catch the light, or slim silhouettes that flatter the ankle instead of overwhelming it.

Some pairs even play with luxury: pearls woven through laces (Chanel has flirted with this), satin ribbons, or whisper-thin gold piping. They’re proof that sneakers can glide from brunch to the ballet without anyone wondering if you forgot to change after yoga.

I’m Not the Only One Switching For Sneakers

I’ll confess, it helps to know I’m in good company. I’m not the only one trading stilettos for comfortable sneakers – some of the world’s most stylish women have made sneakers their signature.

Céline Dion pairs her couture with chunky white trainers, Jennifer Aniston strolls New York in Converse-style sneakers that look effortlessly polished. And how about Sandra Bullock? She embraces neon trainers to brighten her basics. And then there’s Dame Helen Mirren, who rocked bright green sneakers on the Cannes red carpet. Proof that sneakers aren’t just for errands—they’re for every stage, every setting, every woman.

The Starter Pack (Because One Pair Of Sneakers Is Never Enough)

My collection began innocently: one pair of crisp white trainers. They were meant for errands, but they ended up everywhere with me: the gallery opening, the weekend brunch, the flight to Florence. From there, it snowballed:

• The Polished White Leather: clean, simple, goes with everything (Adidas Stan Smiths, Axel Arigato, Veja).

• The Soft Neutral: blush pinks, pale taupes, greys that work with linen and denim alike (Ecco and Cos do these beautifully).

• The Statement Pair: leopard print, metallic accents, or a bold color pop (Golden Goose, love them or roll your eyes at them, always make a splash).

• The Luxury Indulgence: maybe just one, with a logo or embellishment that whispers rather than shouts (Gucci or Ferragamo know how to do this well).

Before I knew it, the sneakers had claimed the prime shelf once reserved for Louboutins.

Why I Don’t Miss the Heels

And you know what? I don’t miss heels. Not one bit.

I don’t miss the blisters that turned every wedding into a test of endurance. I don’t miss standing at a cocktail party, pretending to be fascinated by someone’s story while secretly calculating how much longer I could last before my toes went completely numb.

I don’t miss the way heels slowed me down—literally—while the world marched ahead.

I don’t miss carrying a spare pair of flats in my bag “just in case,” or the guilty little sigh of relief when I kicked my shoes off under the dinner table. I don’t miss cobblestones, gravel paths, or rain puddles that instantly turned stilettos into weapons of self-destruction. I don’t miss the chiropractor visits, the plantar fasciitis, or the faint but constant hum of discomfort that came free with every pair.

But more than the aches and logistics, I don’t miss what heels represented: the old rule that said women had to teeter on four-inch spikes to look polished, powerful, or put together. That myth feels outdated now.

Sneakers don’t diminish me; they liberate me. They let me move faster, laugh louder, and live in the moment instead of worrying about a twisted ankle. They give me energy instead of draining it.

When I lace up my sneakers, I feel grounded in every sense of the word. I can dart across an airport without a second thought, dance at a wedding until the lights come on, or stroll home at midnight without calling a cab in defeat. Sneakers let me say yes to life, instead of “maybe, but only if there’s seating.”

Heels had their season. They gave me height when I thought I needed it, and drama when I thought I couldn’t make an entrance without it. But sneakers? Sneakers give me something far more valuable than inches: they give me freedom, strength, and joy.

And joy, my friends, is the accessory that never goes out of style.

When’s the last time YOU wore high heels? Let us know in the comments below.

Like this post? Support Us or Sign up to our newsletter to get more articles like this delivered straight to your inbox!