My obsessions sneak up on me.
One day, I’m tracking the price of gold; the next, I’m geeking out over the water resistance specs of automatic watches; and then, without any warning, I’m stalking vintage baseball cards on eBay, bidding at the last possible second to try and snipe a killer deal on a 1956 Topps Don Mossi.
So, it is with only mild bemusement that I find myself staying up late at night to watch YouTube videos of a scruffy hipster cutting boots in half to analyze their build quality in absurd depth. Suddenly, I’m parsing the differences between Goodyear welt and blake stitch construction and debating the pros and cons of a leather shank—even though my only boots are a battered pair of decade-old hikers.
What’s surprising isn’t my own weirdness (I’m used to that) but rather how many others out there are just like me. These boot cutting videos have hundreds of thousands of views, and I soon wander into Facebook groups where grown men are, for some reason, getting very angry with one another for wearing their boots with cuffed jeans.
Where did all these Boot Guys come from?
My mom is visiting when my first boots arrive—a pair of Grant Stone Diesel service boots ($395) in Chromexcel leather dyed by the famous Horween tannery. The name of the color is “crimson” but in reality they’re a rich chocolatey brown. I turn them over in my hands, admiring the antique brass eyelets and flawless consistency of the stitching.
They might, I think, be the most beautiful wardrobe item I’ve ever owned.
“Look!” my mom screeches, pointing. “They have a heel!”
“They’re boots,” I tell her. “They’re supposed to have a heel. In fact, these specifically have a leather heel block with a rubber top lift.”
My mom is howling. “Who are you, Tom Cruise?”
I ignore her and try them on. This is my first time trying on the Diesels, as Grant Stone is one of a handful of direct-to-consumer boot brands that have popped up over the past decade. I’m not sure whether the existence of these companies has sparked the growing online community of diehard boot enthusiasts, or if it’s the other way around, but either way, these brands are keeping the art of handmade boot making alive, and my newly converted boot-zealot self is here for it.
I’ve read that the Diesels are supposed to feel like sneakers right out of the box, but I’ve also read that high-quality boots should be a bit uncomfortable at first. If the latter is true, then these might be the best boots ever built. Compared to my pillowy hiking boots, the Diesels feel like blocks of wood on my feet. Especially on stairs, the thick leather bites into my ankles, and I find that I can only wear them for an hour or so. But as I put more miles on them, the boots loosen up, and luxurious folds begin to form in the leather.
I’m hooked.
Next up is Parkhurst, another direct-to-consumer company with a rabid following. The brand is known for its exotic leathers and unique colors, but I opt to keep things simple with a pair of Allens in black vegetable tanned teacore ($418). The teacore effect means that the top layer of dye eventually wears away, creating a distressed, vintage look that is highly desirable for reasons I don’t yet fully understand.
For now, I’m content with the supple black leather, set off by a contrasting natural leather midsole. Boot Guys spend hours debating black vs. brown (although Parkhurst buyers are more likely to opt for colors like spruce, rust, and clover). The consensus is that brown is more versatile, but I’m not sure I agree.
These boots go with everything. They’re classic.
Any sane person would stop here. But I’ve never owned a Chelsea boot, and I’m intrigued. I pick up two pairs: the Ace Marks Troy in brown ($350) and the Jack Erwin Ellis in black ($248). I wear my lace-up boots cinched tight, so the elastic panels and roomy ankles of the Chelsea boots throw me for a bit of a loop. I accidentally get half a size too small in both pairs.
Still, something interesting happens when I wear them. I begin to build my outfits literally from the ground up, not wanting to wear a schlubby hoodie with my new calfskin boots. My mom’s initial reaction, perhaps, illustrates my starting point—a world where any clothing choice fancier than a Carhartt jacket is considered suspect. But now I begin to experiment with my style, dressing up a bit for no particular reason.
I wear the black Jack Erwins to my daughter’s school open house, and one of her classmates comments on them the next day, asking her where I got my “nice shoes.” For a night at the theater, I start with the brown Ace Marks and then toss on a simple pair of slacks and a button-up. It’s nothing runway-worthy, but for the first time, I start to notice what other men are wearing, and it’s very possible that I’m one of the best-dressed guys there.
The bar is low, and it can easily be cleared with the tiniest bit of effort. A nice pair of boots, I’m finding, is enough to make me finally try.
If you know a man who has fallen down the heritage boot rabbit hole, chances are good that Thursday Boots were his gateway drug. The company advertises more aggressively than other online brands, and it has somehow kept the price of its flagship offerings steady at $199 since it launched more than a decade ago. But I opt for the Wingtip ($235) in Color #77, a brown with an intentionally mottled appearance. It’s the sort of colorway that seems to look different in every photo, and I’m a bit worried that they’ll disappoint. But when they arrive, I fall in love instantly.
The wingtips do feel like sneakers right out of the box, and the broguing on the boot instantly elevates whatever else I’m wearing. I put them on to attend my daughter’s basketball games, and random moms start complimenting them. “I wish my husband would wear something like that,” one tells me.
Taft is my chance to go even bolder. The company has its own design language, with creative uppers (including woven textures, tweed fabrics, and even a dragonfly pattern) flanked by more standard leather toe and heel caps. At first, I toy with the idea of a relatively tame black suede or oxblood, but at this point, they would barely stand out in my growing collection. Then, I find myself pulled toward the Jack ($295) in Taft’s Eden colorway: an ornate woven jacquard tapestry of beautiful golden flowers set against a black field.
I buy a floral shirt and wear it with the boots and a navy suit to a friend’s wedding. A few months ago, I would have shown up in the most boring brown Oxfords I could find, but now I’m the guy wearing floral-on-floral. And I totally own it.
The Maine Moc Toe ($329) from Origin swings the pendulum back the other way. Origin, based in Maine, is fanatical about making its products, including jeans, hunting gear, and jiu-jitsu gis, in America. This is something I admittedly do not spend a great deal of time thinking about, but it’s very important to lots of Boot Guys.
When I email the company about sizing, they tell me I should go up half a size, “especially if you plan on working in them,” since my feet will start swelling as I move around. Although I grew up bailing hay and detasseling corn in Iowa, “work” these days means sitting at my laptop and obsessively watching boot videos. Still, I follow their advice, and the boots feel great. I take them for a walk, then wear them to clean out the garage and put together an Ikea dresser. I’m not much of a worker, but when I’m working, the Origins are my made-in-America work boots.
The Baldor 8” Steel Logger ($250) from Chippewa is yet another rung up the ladder of workwear aesthetics. The style is aggressive and, at first, I worry I won’t have the confidence to pull them off. But the logger heel (I can hear my mom laughing) sends my height over six feet for the first time in my life, and it’s as though the boots themselves are giving me permission to wear them. I stride into a PTA meeting in dark wash jeans, a thick gray sweater, and my new loggers—ready to either chop down a Douglas fir or raise money for the eighth-grade trip to D.C.
After a while, my boot collection has become the centerpiece of my wardrobe. The previously stiff leather has begun to mold itself to my feet. I’m a different version of myself in every pair: dapper (bordering on dandy) in the Edens, posh and professional in the Chelseas, rugged in the loggers.
And then, my Nicks Americanas ($669) arrive.
These are handmade and built to order. Nicks is a legendary brand from the Pacific Northwest school of boot making, and the word I’ve most seen used to describe the Americana is “tank.”
The boots are heavier than my other pairs, and the leather is super thick. I’ve read that they have a brutal break-in period, and I expect them to feel like concrete blocks. My feet do feel bulletproof in them, but they’re actually quite…comfortable. The arch support and weight of the boot make me feel firmly planted to the ground in a way that’s a little difficult to describe.
For my leather, I’ve selected brown waxed flesh. My non-boot friends find this name a bit macabre, but it’s just a roughout leather smoothed down with a wax coating. Out of the box, the boots are dark—almost black—and the idea is that the lighter roughout will emerge with wear.
I put dozens of miles on my Nicks, looking for any hint of the nap starting to show, but weeks later, they still look brand new. I keep going. I’m officially a Boot Guy now, and the patina I’m after isn’t something that can be bought or rushed or faked.
I have to earn it.
Beyond Boots
To complement my new footwear, I also replace my ratty old belts and boring denim.
Hank’s Belts takes the same pride in its products as premium bootmakers. The beefy full-grain Everyday Belt ($90) and the sleeker Esquire Premium Dress Belt ($160) are my go-tos.
The mix-and-match strap and buckle kits (starting at $100) from Anson Belts give me what feels like limitless options. And the micro-adjust system ensures a perfect fit every time. My personal stylist at Stitch Fix ($20 styling fee plus the cost of items you keep) helps me fill out the rest of my wardrobe with brown and olive denim and a textured blue sweater.