I’m continually surprised by how many bad boots are on the market. Think about it: these shoes need to go from concept to capital to production with hundreds of steps along the way. Companies need to be formed. Leather needs to be tanned. Websites need to be created. Entire businesses are formed around products that are just plain bad.
There are countless things that can go wrong with a boot and I’ve seen them all: iffy arch support, slippery soles, lousy lasts… and then there are the issues that you can’t pick up on when you’re trying boots on in a store, like leather that creases too fast or heels that detach after just a few weeks. And no matter how many boots I own — and I own well over a hundred pairs — I always gravitate toward a small group of favorites.
Out of every boot I own, these are my ten all-time favorites.
1) Best Boot: Thursday Boot Company’s Captain Boot
- Versatile dress/work boot hybrid
- Wide variety of leathers
- Just $199
This is a really phenomenal boot and despite my eye-wateringly huge collection, it’s the one I wear the most.
The guys who started the company were fed up with the fact that most good boots are expensive simply because of the brand’s value and not because of the actual quality of the materials and construction. They were also after a boot that was neither a dainty dress boot or a heavy work boot — the idea was to make a new kind of boot that you can wear with anything and won’t cost you an arm and a leg.
So Thursday’s Captain boot is in no way an imitation of somebody else’s product. It’s a wholly unique product that’s meant to be the perfect hybrid boot, a combination of dressy and casual that I think completely succeeds.
The shoe also has a 360-degree Goodyear welt that’s subtle and close in to the vamp, so while it’s very water resistant and easy to resole, it doesn’t have any of the chunkiness that you often get with a full Goodyear welt. On top of that (literally) there’s an EVA comfort strip, a kind of foam that’s often used in athletic shoes. It results in a boot that, after a few days of breaking in, feels a lot more like a pair of sneakers than a quality leather boot.
Perhaps the most remarkable aspect of the boot is the price: $199. This is inarguably the best value boot on the market and in my opinion, the best boot, period.
Runner Up: Oak Street Bootmakers’ Trench Boot
- Made in Chicago
- Sturdy construction
The runner up for the best boot overall is the Trench boot from Oak Street Bootmakers.
It’s a beautiful boot with really robust construction, and it’s made in Chicago with leather from the city’s famous tannery, Horween Leather Company. It’s a really sturdy, versatile, and resoleable boot with the kind of design simplicity that lets the construction and materials speak for itself.
It’s also totally made in America (even the packaging is sourced domestically), but at about $460 it’s not cheap, so it’s hard to recommend for everyone. They go on sale several times a year, though, and if you’re happy to get one with a leather sole then the boot is about twenty bucks cheaper.
2) Best Moc Toe Boot: Grant Stone’s Brass Boot
- More versatile than most moc toes
- High quality, vegetable tanned leather
Next up is the best moc toe boot, an absolutely classic casual style that really elevates any casual outfit. The Brass Boot from Grant Stone is a completely unique, very versatile boot from a company that’s better known for making really nice footwear that’s a bit more dressy than this — the brass boot is their first attempt at a work boot type boot.
That might not mean it’s perfect for electrician work so much as it means it ‘s roomy, it’s sturdy, it’s muscular, and it goes great with casual outfits. But this moc toe is just a tiny bit sleeker than your average moc, and I’ve even seen guys say they can wear them with button downs and a blazer as easily as old jeans and a t-shirt.
The Brass Boot is stupid versatile, the leather is spectacular quality (this golden one is Italian vegetable tanned leather that will age beautifully) and it’s a great pick for guys who don’t own a lot of boots and want one pair that pairs well with almost anything.
Runner Up: Red Wing’s Classic Moc
- American made
- Iconic aesthetic
The runner up is Red Wing’s Moc Toe, which is the moc toe of moc toes. My Charcoal ones are my oldest pair of boots and they’re absolute classics. Everyone from Ryan Gosling to Drake has a pair, usually in the golden Oro Legacy leather that matches with practically everything.
I prefer the Brass Boot because of its leather quality and, again, I think the silhouette is more versatile — you simply cannot dress up a Red Wing moc toe — but Red Wing’s is cheaper at $280 to $290 (depending on the leather), plus it’s made in the USA.
3) Toughest Boot: White’s MP Sherman
- Handsewn stitchdown construction
- Very thick, tough leather
- Modeled after military police boots
- $550 – $600
It’s important to note that I’m talking about the toughest fashion boots, here — I’m not looking at boots that can withstand magma or fire, rather boots that look great when worn out on the town and are still tough as nails when they need to be. For that, I had to go with White’s.
Made with very thick leather, multiple leather midsoles, and a vegetable tanned leather shank, the boots are so substantial you’d swear you’re wearing a cow on either foot. But it’s not just the weight that matters to purists: these boots are made with handsewn stitchdown construction, which is far more laborious and demanding than the standard Goodyear welt found on the other entries on this list.
For guys who appreciate craftsmanship and durability, White’s can’t be beat.
Runner Up: Truman Boot Company
- Made in Oregon
- Wide range of cool leathers
An all American brand founded in Pennsylvania and now based in Oregon, Truman Boot Company stands out in the marketplace for its spectacular construction, pretty good value (they’re practically all under $460, a good deal for made-in-USA boots), and their leathers.
My boots are made with the company’s flagship Java Waxed Flesh, a roughout leather from Horween that’s ultra durable and scratch resistant, and it ages beautifully, lightening over time and revealing a golden nap underneath. But Truman has the most innovative leathers in the game, from bright red to sky blue, deep green, and more.
When I wear a pair of Truman boots I feel indestructible and, well, cool. There, I said it.
4) Best Luxury Boot: The Alden Indy
- Extraordinarily comfortable
- Made in New England
- Worn by Indiana Jones
“Luxury boot” doesn’t necessarily mean “dress boot;” everything on this list can be worn casually. I’m talking about boots that are truly legendary in the industry for their history, their quality, and, sure, for their price. Both boots in this section come from companies founded in the 19th century and both cost well over $500.
The first is the American made Alden 403, better known as the Indy, because this is the boot Indiana Jones wears in all his movies. If that’s not the coolest hook ever, I don’t know what is.
It’s a really cool design that’s unique and eye catching, yet subtle. The boot also has a storm welt for extra water resistance (handy when you’re swimming onto German U-boats), plus Alden makes them in New England from start to finish. Founded in 1884, the company has a surprising history of making orthopedic shoes as well, and the Indy is often recommended by podiatrists for people with foot pain because they’re such comfortable, supportive shoes.
Especially if you’re on your feet all day. And especially if you need to survive a nuclear explosion in a fridge.
Runner Up: Carmina’s Chelsea
- Elegantly made in Spain
- Luxurious French box calf leather
The next best luxury boot is Carmina’s Chelsea. This is a boot with a very rich history: it’s made on the Spanish island of Mallorca and the family’s history of shoemaking there stretches back to 1866.
The company is well known for their elegant lasts. A few highly regarded aspects are that the upper is made with box calf leather, a celebrated French calfskin that’s known for its smoothness and vibrance; the sole is three layers of leather, which many consider the ideal construction for softness and comfort; and there are many interesting touches from their precision craftsmanship like the sole’s high stitches per inch and closed channel stitching.
These high end components can be seem a little complicated for the average joe, but I go into more detail in my full review. Suffice. it to say, they’re widely considered to be very good value at $525.
5) Best Chelsea Boot: The R.M. Williams Comfort Craftsman
- Made in Australia
- Yearling leather is great balance of soft and tough
- Versatile aesthetic
The Chelsea boot is a fundamental part of any guy’s wardrobe and the best has to be R.M. Williams. Now, you might think I’m biased because I am Australian and every single Australian owns a pair of these boots, but they have a solid reputation here in the United States as well.
The yearling leather is a great mixture of soft and tough, and I’d say it’s the most versatile Chelsea you can get. It’s not uncommon to see them worn with a suit in Australia, which is where they are proudly made; in Manhattan dressing up Chelseas is a tad more controversial, but these boots can definitely be worn with a t-shirt or with a blazer.
Not everyone likes the slightly square toe but they’re insanely comfortable (I sometimes forget to take them off when I get home), they last forever, and Hugh Jackman does their commercials, so ~$500 really isn’t that much when you think about it.
Runner Up: Taylor Stitch’s Ranch Boot
- Extra water resistant construction
- Robust, casual aesthetic
The final boot on this list is also the most underrated: the Ranch boot from Taylor Stitch.
Taylor Stitch is a clothing brand, not a dedicated footwear brand so that might be why everyone slept on this boot upon its release — but it’s really solid. The design is great, the leather is tough, the sole is grippy, there’s some firm but supportive foam in the insole, and the boot has a storm welt like the Alden Indy for extra water resistance.
They’re simply terrific daily beaters, a hair more rugged looking than R.M. Williams but much cheaper.
I haven’t tried every boot on Earth, but I’m very confident in my picks for the best boots on the market right now. I took into account value, comfort, quality, fit, and aesthetics to land on these five and while I believe any of these would be a great addition to a man’s wardrobe, I firmly believe Thursday’s Captain Boot is the best of the five.
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