The Boots Still Fit, the World Does Not

When I was nine years old, growing up in Montreal, I used to take a shortcut through a frozen field to get to school. One winter morning, the ice gave way beneath me. I wasn’t swallowed whole—just knee-deep in freezing water—but I remember the shock, the panic, and the sloshing weight of my snow boots filling with icy sludge. I trudged the rest of the way to school in those soaking boots, and then through the entire winter. They never dried, not once.

But I never told anyone. Certainly not my mother. She was raising three children on one slim salary, and everything in our house had to last until it absolutely, unquestionably didn’t. Those boots were meant to stay on my feet until I outgrew them, not until I fell through a field. So I kept quiet and walked on.

My mother was the kind of thrifty that comes from necessity, not a hobby. She sewed all our clothes. To save money, she’d buy one dress pattern and enough fabric to make the same dress three times—one for each daughter. Meanwhile, Montreal in the 60s was a fashion carnival. Every day on my way to school, I passed bold, psychedelic fabrics in storefronts, platform shoes, daring new silhouettes. Fashion was changing fast, and I couldn’t wait to grow up, earn my own money, and finally choose what went on my back.

Funny how life works. In my teens, I left home without my family’s blessing and moved across the country to Vancouver. Suddenly, I was working, studying, and budgeting on my own. No fashion shows on the street there—just rain and practicality. That’s when I discovered second-hand shops and vintage stores. I altered thrifted pieces, added zippers to sleeves (it was the punk era, after all), turned dresses into jackets, jackets into dresses, and sometimes bought garments just for the fabric. I fell right into step with a whole generation rejecting consumerism—whether by ethos or by necessity.

Eventually, I landed in Milan in the year 2000—fashion capital of the world—and my thrift-store habits didn’t stand a chance. Milan seduced me with craftsmanship, leather, tailoring, and boots that seemed to whisper my name from shop windows.

Ah, boots. My lifelong companions.

Between growing up in Canada, where winter lasts nine months, and working more than a decade in film, where steel-toed boots are mandatory even in August, boots became part of my identity. But the frozen-field incident left its mark: for years, I had recurring dreams in which I was in a crowded station or a grimy public bathroom and suddenly realized I was barefoot. I’d wake up anxious and exposed.

Perhaps this explains why I started collecting boots—especially cowboy boots. Short, tall, plain, embroidered—I loved them all. They were sturdy, dependable, protective. The grown-up version of the security blanket. I filled a walk-in closet with them and polished them like treasures.

Then, in 1999, preparing for my move to Europe, I sold nearly everything I owned—including the entire cowboy-boot collection. Sometimes, even now, I still regret it. Especially considering what boots cost today.

Italy’s warmer winters didn’t stop me for long. I soon began building a new collection, this time with beautifully made-in-Italy leather. I even wore boots in summer until one brutal heatwave convinced me sandals weren’t a moral failure. When I bought my scooter, thigh-high boots became my winter favorites—they protected my legs from wind, cold, and the occasional Milanese pothole. To this day, I feel a little flutter when I see a good pair of thigh-highs, as if passing an old lover on the street.

But as my closet grew, something else grew too: a small, insistent voice whispering “You don’t need all this.

Travel made it easier to hear. Whenever I packed only a carry-on, I realized I was perfectly content with just a few well-chosen pieces. Even then, I still brought things I never wore. So, slowly, I started giving things away—a jacket here, a dress there—to a young mother and her teenage daughter who lit up every time I arrived with a bag.

At the same time, I began noticing a troubling trend: the newer the item, the faster it seemed to fall apart. Clothes I’d bought 20 or 30 years earlier still looked fresh. But newer pieces? Worn out, pilled, stretched, frayed—or literally disintegrating—after only months. I tossed boots whose soles separated from the uppers, jackets that flaked, faux leather that peeled on its own while hanging untouched in my closet.

Some things weren’t falling apart from wear. They were falling apart from being made to fall apart.

Fast fashion had exploded in the early 2000s, right around the time I moved to Milan. Brands released hundreds of new styles every week, producing massive quantities of cheap garments made from low-quality synthetic fabrics. Polyester replaced cotton, cost replaced craftsmanship, and speed replaced quality. Clothes became disposable—not because people wanted them to be, but because they were built that way.

My mother—who spent her life sewing—would have called it sacrilege. She was a fabric purist long before it was trendy. She used to run her fingers over a bolt of cloth and immediately know if it was worth her time. Synthetic fabrics made her skin crawl. Today, synthetics are more sophisticated, but even so, a lot of what we buy is simply not meant to last.

The real problem? We’ve gotten used to this. The average consumer buys 60% more clothing than fifteen years ago, even though those items last half as long. We replace instead of repairing because many things can’t be repaired. Try fixing a faux leather boot that has peeled off in brittle flakes, you can’t. Try resewing a fast-fashion jacket with seams coming apart—there’s barely anything to stitch into. We’ve quietly lost our right to repair.

And the consequences aren’t just financial. They’re environmental. Social. Psychological.

Have you ever stared at a stuffed closet and thought, I have nothing to wear? That’s not a fashion crisis—that’s a clarity crisis. Most of us wear the same 20% of our wardrobe 80% of the time. The rest becomes forgotten, guilt-inducing clutter. And still, the cycle continues: more choices, less satisfaction.

Eventually, I hit a wall. I realized that the items that brought me the most comfort and joy, the things I used over and over, were the well-made ones. The ones that lasted. The ones that recalled my mother’s lessons about durability, care, and value. And the ones that weren’t well-made? They made me feel wasteful and foolish.

Slowly, I started choosing differently.

Instead of asking Do I want this? I asked, Will I wear this at least 30 times?
If the answer wasn’t a solid yes, I walked away.

I started to check seams, fabric content, and construction. I stopped buying “bargains” that weren’t bargains. I bought fewer but better pieces.

Quality, I realized, isn’t just about spending more; it’s about spending thoughtfully. It’s about recognizing that craftsmanship has a value, that longevity is a form of savings, and that comfort, real comfort, comes from things made with care.

In a way, the world has circled back to what my mother knew in her bones: that a well-made garment is worth its weight in fabric. She grew up at the end of World War II, married with three children by 24, and had no room for waste. Even when she had money later in life, she remained careful, practical, and resourceful. She used things until they couldn’t be used anymore, not because she was deprived, but because she understood value.

I didn’t always see the wisdom in that. I had to live through decades of shopping, collecting, purging, regretting, rediscovering, and relearning before I understood the lesson she quietly embodied.

Today, I’m proud to say I’ve healed from the compulsive shopping phase that swept so many of us up over the last two decades. I still love boots—boots will always have a place in my life, but I love them differently now. Not as trophies or trends, but as companions meant to last and be cared for.

The boots still fit.
But I’ve changed.
And in a world where so much falls apart too quickly, choosing what lasts feels like the truest luxury of all.

Published by Maddalena Di Gregorio

“I kept always two books in my pocket, one to read, one to write in” Robert L. Stevenson

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