They tell me it has been twenty five years since Winston & Wilfred first set needle to cloth. I find that hard to believe. Some mornings, when I unlock the workshop door and the scent of cotton and pressed wool greets me, it feels as though time has folded in on itself. The same sunlight still slants across the workbench. The same hum fills the room as the sewing machine wakes.
We never set out to chase fashion. We simply wanted to make a cap that would last a lifetime, the kind you could wear through rain and shine, through age and memory, without it losing its shape or soul. We wanted something steady. Something honest.
In those early days, money was scarce, but conviction was not. We worked late into the night, guided more by instinct than by plan. The room would fall silent except for the scrape of scissors, the hiss of steam from the iron, and the faint smell of tea cooling beside the machine. That was the beginning of Winston & Wilfred, not a grand idea but a humble desire to build something true.
Every stitch that left our hands carried a promise that no matter how much the world changed, craftsmanship would remain our language.
Where It All Began
Our story began beneath the watchful eye of Master Harrington, the man who taught us to respect the patience of thread. His workshop was dim and crowded, walls lined with rolls of tweed and linen, wooden shelves stacked with hat blocks, and an old radio humming quietly in the corner.
He had been making caps since before either of us were born, and he could spot a lazy stitch from across the room. His lessons were simple but unyielding. Measure twice. Cut once. Never rush the work. A cap that leaves your bench carries your name, so see that it does so proudly.
Winston, ever the perfectionist, absorbed every word. His cuts were exact, his folds precise, his eye for proportion unmatched. I, Wilfred, was a different sort. I wanted to build caps that could weather a storm, that could be crushed in a suitcase and still come out looking respectable. Harrington called us opposites, but I think he secretly enjoyed our sparring. He said we reminded him of his own youth, ambition tempered by care.
It was in that little room that our friendship took root. We shared more than tools. We shared the same belief that a man’s craft should outlive him.
The First Cap
Our first cap was stitched on a borrowed table under the faint light of an old lamp. The fabric was leftover navy twill, soft at the edges and stubborn under the needle. We argued for hours about how the brim should curve, whether the lining should be cotton or satin, and how wide the top panel ought to sit.
When it was finished, we placed it on the bench between us and stared at it as if it were something sacred. The seams were uneven, the inside label crooked, but it held its shape. It looked right.
That cap became our measure for everything that followed. We wore it ourselves, traded it back and forth, took it out in rain and sun to see how it would hold up. After a year, the fabric faded beautifully, the brim molded to the hand, and we knew we had found our way.
Even now, that first cap rests in the corner of the workshop, faded, frayed, and irreplaceable. It reminds us that all good things begin humbly, and that perfection is not born overnight but built stitch by stitch.
Built to Endure
From the start, endurance guided every decision. A cap, in our eyes, should not be something bought and forgotten. It should accompany a man through his years, softening with use, carrying the quiet story of his life.
We reinforced our seams so they would not fray with time. We sourced cottons and corduroys that grew softer but never thin. We hand cut each brim, not for speed but for balance, so that it sat comfortably no matter the weather. We chose brass fittings because they aged with dignity, taking on a patina that told its own tale.
In the workshop, we used to joke that each cap carried a bit of its maker’s soul. Winston would laugh at that, but I think he knew it was true. A craftsman leaves a piece of himself in every item he finishes. Over the years, we have made thousands of caps, and I like to think a small part of us travels with each one.
We have never chased trends. We have never cut corners. What we began with patience, we continue with pride.
What Twenty Five Years Really Means
To some, twenty five years is simply a number. To us, it is a life’s work measured in fabric, thread, and patience. It is countless mornings spent in the same workshop, the air warm from the iron, the sound of scissors cutting through cotton, the smell of tea steeping nearby.
Our mentor taught us that a cap carries its maker’s patience, and he was right. Every hat tells the story of its creation, the concentration, the silence, and the pride when it is done just right. We have watched trends rise and fall, seen factories replace people with machines, but no machine has yet learned to sew with heart.
We have seen our caps travel the world. Some come back to us for repairs, carrying the faint scent of years gone by, others arrive in photographs sent by customers who tell us their cap has become a part of them. Those are the moments that remind me why we began.
Now, as we hand our knowledge to younger craftsmen, I see in them the same fire we once had. They are learning the value of slowness, the meaning of quality, and the satisfaction that comes from making something meant to last.
We are moving toward finer materials like organic cottons, gentle dyes, and sustainable packaging, but our spirit remains unchanged. Honest work, patient hands, and a cap that sits just right.
Customer Reviews & Our Loyal Customers in Craft
Over twenty-five years, we have met countless gentlemen and craftsmen who wear our caps not as fashion, but as part of who they are. Each one reminds us why we began: to create something that could travel through time and still feel like home.
These customer reviews reflect what matters most to us: loyalty, craftsmanship, and the quiet satisfaction of a cap that fits just right.
Here are just a few of the many loyal friends who have shared this journey with us.
A loyal supporter for twelve years, our friend from Boston, USA has built a small collection of our caps, each one tied to a memory. In his review, he says they have traveled with him from snowy winters in Maine to summer walks along the coast, always reliable and always true.
For more than a decade, this gentleman from Ontario, CA has worn his cap while playing his ukulele and spending quiet evenings by the lake. His review tells us it fits like rhythm itself, steady and familiar. It keeps its shape through the years, just like the songs he plays.
For twenty years, this Yorkshire, gentleman has worn his cap through every season. He once told us, “It has been with me through weddings, walks, and winters.” That is all a maker could ever hope to hear, the kind of review that reminds us why we craft each cap by hand.
A Word of Thanks
If you have ever worn a Winston & Wilfred cap, you have carried our story. You have given purpose to our work. Every time you tipped your brim to the sun, every time you packed it for a journey, you became part of what we started all those years ago.
We owe this milestone to you, our customers, our craftsmen, and our friends. Without you, there would be no reason to keep the lamps burning in the workshop or the irons humming on the table.
For twenty five years, you have trusted our craft, believed in our story, and proven that quality still matters. For that, I offer my sincerest thanks.