Let me state for the record, I absolutely did not spend £625 on a pair of goddamn boots. I got these at the Crockett & Jones factory in Northampton where they also sell their seconds—shoes that aren't deemed 100% perfect and are sold at a big discount. I think I got these for £250, which is still insane, but the defect in this pair was an almost imperceptible scratch on the toebox.

Whenever I visit my parents in the Northamptonshire countryside, I grit my teeth to resist the urge to wander into one of Northampton’s world-renowned factory shops, where I inevitably end up buying seconds because I’m a cheap bastard—but a luxury, handmade kind of cheap. Church’s, Barker, Joseph Cheaney, Loake—the list goes on, from the more commercial Dr. Martens to brands you’ve probably never heard of, let alone afford, like John Lobb. One particularly grim day, I decided to head to the Crockett & Jones factory in hopes of finding my grail boots as seconds. Previous visits had left me empty-handed, with the staff explaining that the Dark Brown Scotch Country Grain Islay boots rarely appeared as seconds and, when they did, they were snapped up the instant the doors opened.

We parked up down an old-looking side street and walk towards one of Northampton's original shoe factories. Big red-brick buildings that have never needed to be updated since the mid-to-late 1800s each housing ancient machinery to hand-make shoes and boots—I'm trying to romanticise Northampton because the rest of the town is a total shit heap. Once inside the small shop, I immediately scanned the room for the fabled boots that were made famous by Daniel Craig's James Bond during some countryside shootout in the movie Skyfall, and let me tell you, I'd have shot my own feet off after 5 minutes if I were James Bond wearing these boots, but we'll get to that. Not spotting them, I sidled up to the member of staff staffing the joint and asked about them. Fully expecting the usual response where they'd tilt their head somewhat in an "aww you poor thing" type way, she said she thought she saw some next door in the factory. My pupils dilated like I had been given a shot of hardcore street drugs as she called someone presumably on the factory floor. It turns out that someone she called was one of the descendants of the founding families. Same last name and everything (either Crockett or Jones, I can't remember). Stunned somewhat that something as old as Crockett & Jones, 1879, was still in the family, the kindly member of staff asked me to wait as the Islay boots I had been searching for were among boxes of the other non-prime-time products in the adjacent room.

The boots radiated a quality I hadn’t seen before in anything I was about to buy. Sure, they’re in the same league as other brands selling boots and shoes for a mountain of money, but these had already claimed the throne in my collection. Even standing next to my other pair of Crockett & Jones Islay boots, they looked and felt leagues better. The Scotch Grain leather held its shape far more elegantly than the strange crazy-horse-type leather of the other pair, which sags listlessly like a forgotten shopping bag full of decaying oranges in the corner of a dusty room. The rubbing, creases, and folds gave the Scotch Grain Islays a beautiful, aged look that promises to look even better with time—unlike my other pair, which just looks tragically worn whenever a new crease or scuff appears.

I decided to take these boots for a long country walk along with my dog. People online were going on about how they trek across landscapes of all shapes and sizes in these boots and everything is just great, but after a year of wearing these boots, I couldn't think of anything worse to happen to me than wearing them and doing that. Still, I thought I'd better grow up and give it a go.

I won’t get into the lovely walk I had, because after just two hours of tromping through the wilderness, my feet felt like they were in a chemical fire. For the first year, I convinced myself I was still “breaking them in,” as you do with all handmade shoes. The stacked leather heel and traditional cork filler mean a fair amount of pain until the shoe gradually molds to your foot. But these boots, I’m afraid to say, will never be comfortable for me. After some investigation, I identified the main culprit for this perpetual discomfort: the Dainite soles.

My other Islay boots have a Vibram sole, the same all-terrain style of sole found in Doc Martens or Solovair boots (the original makers of Doc Martens and 100% better in every way) where there's a slight squish on the chunky rubber bottoms and actual grip. And speaking of grip, there's the rounded-up amount of zero for the Scotch Grain Islays. Slightly damp pavement? Prepare for absolute ice-skate shenanigans. Slightly cold floor? You'll be slipping into next week. When entering a new biome of floor, I have to stand still and twist my feet about like Dorothy tapping her heels together to gauge how much of a supremely careful walk posture I have to adopt in order to get anywhere. I hate it so much. The fear of slipping on every walkable surface ever and then to have my feet feel like elephants have repeatedly stamped on them is not something I can excuse after dropping a king's ransom's worth of coin to acquire them, even if they are a pair of seconds. They're also able to sprain and possibly snap your ankle at a moment's notice. Because the bottoms consist of a standard cork filling, a slab of leather welt, and then the fabled Dainite sole, stepping on an uneven surface like a cobbled pavement or a loose stone will shunt the entire boot off balance and rock your ankle into a medical emergency. There's no give or flex at all, which renders them totally useless for off-roading. Trust me and my smashed-up ankles on that one.

A few weeks later, once my feet barely recuperated, I was off to Istanbul—a city where no single street is horizontal. I thought to myself as I hastily packed at 2 am before heading to the airport at 3 am knowing full well I had over a week to pack properly, "I know what—I'll just bring my little boots and no other appropriate footwear for Istanbul, home to the steepest hills on Earth." The last time I went, I wore the boots during the travel and promptly kicked them to a dark corner and changed into some trainers once I got to my room. But not this time. "These boots were made for rugged use with their storm welt and high-quality craftsmanship," I told to myself, unconvincingly, trying to push aside the crescendoing memories of foot pain from wearing them even for just a few hours in an office.

After the unforgivingly solid floors of two airports where stamping as hard as I could barefoot would've made my feet hurt less, I arrived in Turkey at noon local time and spent the entire day perambulating up and down the comically steep streets, going from place to place to eat, drink coffee, and be merry—all of this on two hours of sleep. Maybe it was my being almost high on sleep deprivation but I no longer noticed the uncomfortable throbbing in my feet. All I noticed we how damn good those boots looked, and how nobody else in the whole of Istanbul was wearing anything other than trainers, the fools.

The next morning, I was up before the sun. I quietly stepped out onto the balcony, waiting for the buildings and cat-dotted streets to come into color and for the city’s early risers to start weaving through the narrow alleys. Sipping my cafetière coffee and glancing down at my boots, I thought, “Today will be truly magnificent. I am beside myself with positivity in its most absolute.” Once again, I had convinced my brain to fool myself. After half a day of walking about, I had to hobble into the nearest athletic clothing establishment and spend actual money on a pair of futuristic footwear.

By this point, my nervous system finally caught up with itself after a short reboot during the night. My feet felt as if they were within a time-warped slow-motion explosion whilst being hammered to fragments by robotic blacksmiths—I had never felt pain quite like it. I stuffed the boots in my bag and wore the sneakers out of the store. This, however, caused a different kinda of pain as I'm used to wearing boots, so cushioned inner-soles/soles make me feel as if I'm walking on a waterbed and therefore I have to use muscles in my legs I never knew existed to stabilize myself. Still, I relished this new feeling as my feet were now being gently massaged upon each step.

I do feel sad that I won't be able to see these boots grow up. They'll outlive me, mainly from the sorrowful decision that I refuse to wear them much. Wearing a pair of boots that shows everyone you mean business just isn't worth the distress your feet will go through days after the fact. Yet, they look so good that I forget all we’ve been through together… and thus, the remorseful and painful cycle begins anew.