I spent several evenings prior to a New York City trip toiling in the doldrums of the internet's finest footwear retailers, searching for a suitable pair of Derbys. I knew what they looked like, the infamously traditional British brands, and the American ones that followed soon after. I had never owned a pair of well-made shoes before, having only donned legendary, but more disposable, G.H. Bass Weejuns in my teens, certainly with a suit I was meant to grow into. I had grown fond of the black patent leather loafers until their weathered demise the year before last. In the shallow years preceding this newfound resurrection in footwear interest, I insanely bought any Bragano woven leather loafer within a size of mine on eBay. I liked the folk-country style and thought the now-defunct Bragano had a smattering of good designs to offer. Options were quite slim for the amount of coin I was willing to shell. White ones, brown ones, and a few black pairs later, I only really fell in love with one pair. A brown pair of quality leather, I had the soles fixed once and wore them till they were frayed and paint-stained. I was forced to surrender them as I could feel the judgment in my father's eyes as we walked side by side. My father has claimed ownership of at least ten pairs of Bass Weejuns during his sixty-three spins on earth. I have retired from buying shoes from eBay. I need to try them on first.

A Derby shoe, in my mind, has been in style since its inception and is a timeless design fit for a moderately repressed old-fashioned bloke like me. I planned to buy them in New York as the multitude of options marred a bleak Toronto market (Lost & Found is good). Sipping burnt orange pekoe, I came across a brand from France named Mephisto. A brand whose image, website, meagre content stream, and general shoe designs were primed for an overhaul by any brand development professional. It needs the top-tier treatment and some ostentatious collaborations to fit back in on the playground. Great logo though. A Mephisto Derby titled ‘Marlon’ mirrored the image in my mind, with pebbled black leather and 100% caoutchouc sole, which was French to me. I knew no one with my middling awareness of fashion would own a pair of these and I liked that. They were expensive but were no Churches, and my mind, body, and wallet were ready. I moseyed into Saks Fifth Avenue and saw the shoes in a subprime display location, which made me think the footwear buyer knew what was up, and the merchandiser did too. Figuring I would venture to the source, I trudged up to the Mephisto NYC locale and found exactly what I expected. A dated, unassuming store with shoe-lined beige walls featuring styles I would gander a guess are big in Europe? You tell me. In the fastest transaction the sales representative had ever settled, I had my shoes and went back to my hotel. I brandished them to my brother, he nodded in agreement, and we went for dinner, cautiously aware I was wearing the most expensive shoes I had ever purchased.

Stamped in the sole were the words Goodyear Welt. Someone like myself, leaning above-average intelligence when the sun is shining, might put two and two together and determine the Goodyear tire brand provided the rubber for the shoe's sole. A collaboration I was not hard-pressed to make sense of. A Goodyear welt is a strip of rubber, plastic, or in my case, leather that runs around the outside of a shoe above the sole. A Goodyear constructed shoe entails a shoe built by sewing the upper to the insole so that both parts are married. The upper and insole are then sewn to the leather welt, which outlines the entirety of the shoe. The sole is then cemented/glued and sewn to the welt. In some cases, the heel is added last. The primary reason for this construction is the ability to repeatedly re-sole the shoe without damaging the upper/insole whilst keeping the shoe's durability intact. Unlike shoes manufactured by cheaper methods, they can forgo the garbage receptacle when the soles are past due. I was, however, not far off with my early inkling concerning the Goodyear name. Charles Goodyear was a self-taught chemist and industrial engineer who invented vulcanized rubber, receiving a patent for his work in 1844. Charles Goodyear's son, Charles Goodyear Jr, who frequented shoe factories, paid homage to his inventor lineage and developed the Goodyear welt sewing machine revolutionizing footwear manufacturing. This machine requires one skilled craftsman at the helm of the device (constantly at risk of dismemberment). Frank Seiberling, the founder of Goodyear Tire and Rubber Company, named his business after Charles Goodyear.

I have a transitory obsessive personality fixating on the next subject that yearns to take me under. After buying these shoes, I put on my horse blinders and spent my free time learning why shoes are the way they are and who made them this way. I didn't stray too far from Derby’s, Loafers, Brogues, Wingtips, Oxfords, etc., between the preppy and sartorialist stanchions, which I guess I fit. I don't mind preppy; I don't like sartorialist, I don’t know if that makes sense. Looking at all brands and websites, ranging from Ssense to ancient sites looking primed and ready for Web3. A legion of quality shoe peddlers lies beyond the search button, which goes without saying as there are about twice as many feet as there are people. I like my new shoes and wear them often, only switching between them and a blake-stitched Paraboot loafer as I banished my eBay shoes to the corner. I only wanted to wear leather shoes. I sailed my ship right past the Steve Jobs trainer trend as it sailed right by me, and I was done with converse. I was over comfort, I wanted pain, I wanted to suffer for fashion and pay a high price for it.

My brother recently started working in fashion, and the majority of our nonsensical chatter fluctuates around the all-encompassing full-court press of ‘sustainability’ or now titled ‘responsibly’. He recently purchased ‘The World Is On Fire But We're Still Buying Shoes’ by Alec Leach, a former fashion editor and creator of sustainable fashion platform @future__dust. An eloquently approachable book which delves into the facts and psychology of the fashion industry's sustainable woes while we wait on tenterhooks, wondering what this apoplectic earth will foist upon us. The book entails two sections, analyzing what is behind the issue and providing plausible ways to curb our impact. I read it in a day and have sponsored a seat in the choir he's preaching to for quite some time now. He was once greasing the wheels of the fashion machine until his ‘a-ha’ moment struck him with a more introspective approach to consumption. The lingering thought I mulled over was how do you get this book into the hands of someone with a minute sense of self-awareness and ability to reflect upon themselves to change. I'm not sure people change unless something dramatic happens to them, and sustainability won't drastically change until someone like Kimmy K decides to pull up her Skims and lay down the hammer. Until then, I'll continue to blather.

Being engrossed in Goodyear Welted shoes, a latent thought surrounding footwear consumption and, more broadly, fashion was bubbling in my cerebrum. With most Goodyear welted shoes, you purchase quality materials inspected by real human eyes. The shoe's construction may have up to one hundred processes completed by real human hands. At the end of the journey, you hopefully have a prideful product ready to accommodate real human feet. Having humans impact the manufacturing of any clothing item in a consciously positive way makes them fit just a little better. Humans are the storytelling animal, it's what we have done since pigment inked stone. Good, bad, long, and short stories lure us, and when we look at clothing, we desperately require a long story and, God willing, a good story, ideally with a love interest or two.

Leonard Cohen’s ‘Famous Blue Raincoat,’ a Burberry trench that accompanied him through his escapades, was worn until the cuffs were frayed and repaired with new leather. The raincoat sat within arms reach as he relayed bluntly sincere locution on paper to be sung in his nasally baritone seeking to capture some semblance of truth. An NYC construction worker who left the subway before me at West 81st Street whose camel-coloured steel toes had their one-and-a-half-inch heels worn down to mere millimetres on the outside, invoking a wedge shape fit to be a doorstop. The wear reflected someone who was clearly bull-legged, had retained the boots for a long time and required this item to do their job as he did accomplish his. I can only speculate, and my mind will run, but I find pieces like this much more interesting in a democratic sense because they mean something more than price-tag or function, they are there through the ebbs and flows of everyday life. They aren’t clamouring for attention's sake, are devoid of vain stories, and implore me to become quizzical about the owner's love for the item. Whether culturally relevant or not, ranging from a labourer's boots in NYC to the famous blue raincoat, both are well made, with stories to tell, and both did a tremendous job in avoiding the landfill till the very end. When my Mephisto’s and I reach our bitter end, historians will write about this article and the extreme exertion I underwent to form coherent sentences in my native tongue.

I started to look at this footwear purchase with a sense of commitment, putting my money where my mouth is instead of my now pebble leather-clad foot. Would I like this shoe in two years? What about five years? What about when I'm old and gray? What if a trend makes Derbys the official shoe for friendless malcontents? I think that would be a stretch, if Plain Jane were a shoe, she’d be the ones on my feet. What if it wasn’t a stretch, and we had to reason with our future selves and the anti-human theory of being ‘content’. How would we feel opening a closet in a few years to look at the items that define our visual language? Would the law of diminishing returns come swooping in and infect the things we knew were a timely gamble or a flash in the pan? I have been a victim here more than a few times and have a lime green canvas Polo bomber that looks at me daily with the sad eyes of neglect. I have never worn it. Trends are environmentally malignant, but in its kingdom lies the land of green milk and green honey. A juxtaposition I enjoy regarding this concept is highlighted in the creative directors of the world's largest fashion houses. They often dress in a subdued uniform manner featuring a through-line of consistency and seemingly quiet confidence that lacks in the entrapment of trends. There is much power hidden in being sure of your tastes, and even more in authentically standing behind them while the consternation of misrepresentation and FOMO hover mere inches above. I wouldn't have been able to ascertain the identity of Casey Cadwallader, due to his pedestrian look, in a crowd had an online editorial about his work not been shared with me. Trends are inevitable; it's what makes life exciting, makes business happen, and feeds people. It would be insane to say I won't dip a little hedonistic toe into the next trend I fancy. Observing it with a more thoughtful approach and a long-run approach seems very just in this day and age.

Since my first pair of Goodyear Welts, I bought a second. A pair of Trickers, on sale, again something that won't send me down the runway, but they were a part of this new ethos I was trying to wrangle. Timeless, exceptionally well made, and primarily focused on durability. The top-class leather of the shoe will, over time, crease and fold in areas it sees fit in relation to the foot's innate movements. The character of the leather will become exceedingly marked, reflecting how the way life is lived. As your skin requires hydration, leather does too, and with the help of a cedar shoe tree, moisture is managed and its posture abetted. In twenty years, let's hope the creases in the leather are more profound than the lines on my face. I like a product you can truly own, is supposed to be used, and requires respect. A mutual agreement you enter where if you take care of the item, it will take care of you. Once the particles of the rubber or leather are strewn throughout your neighbourhood, you can simply have the old soles replaced. No need to inject more energy into making a new product, emit more gasses, and create any more wastewater (all negative aspects the fashion industry contributes to like they are going out of style). If you treat them right, they will last forever. Yes, good-quality items are more expensive, but how many pairs of shoes will you forgo by buying one quality pair? What are the exact implications of creating more new shoes? I tried to get McKinsey to figure out these questions and more, but they have requested I stop calling.