Our favorite fall boots based on quality and versatility.
Dark, tailored denim. A well fitting oxford shirt. A refined pair of boots. There are only a few things we feel absolutely confident in calling an “essential” for a man’s adventure into dressing well. More so than a navy suit or a v-neck sweater, a great pair of boots has the ability to span casual to dressy outfits in a way no sneaker or dress shoe ever can.
What follows is our list of the best of the best, our favorite boots that have impressed us – some pairs going back to 12 years. They feature the best construction methods and leathers, and regardless of your personal style, you’re sure to find a pair of boots that will work hard for you for years to come.
Make no mistake, many of these boots are at a buy once, cry once price. But to quote every grandfather ever, don’t skimp – when possible – on things that separate you from the ground: tires, shoes, and mattresses. Fortunately, there is a spectrum of quality (and price) for men’s boots that prioritize different attributes. What follows is expansive, over 4,000 words, but our guide will help filter those different attributes based on your needs to make sure you find a quality boot for your lifestyle.
Primer Partner Pick:
Thursday Boot Co. Captain
Thursday Boot Co. ($199)
Generally you’d think of a relative industry newcomer as having higher prices and less options, yet Thursday Boot Co., which was founded in 2014 offers more styles, colors, leather types, and sizes (size 6 to 16) at a lower price than any other boot brand on the list. How is this possible without sacrificing quality or price?
Thursday was one of the first “direct to consumer” men’s style brands that first became possible as a business model in the last decade, which allows them to cut out the business textbook markup standards. They focus on creating their whole line in small batches, avoiding the need to store (or clearance) unsold inventory. “We make our boots literally side by side Red Wings, Wolverines, Lucchese, and other top quality brands. Our leather comes from the top tanneries in North America,” co-founder Nolan Walsh told Primer in 2016.
The Dark Olive Suede Captain has been one of our longstanding and most worn boots since first getting them in 2018. The dark olive reads like a brown with a slight olive cast to it and is effortlessly paired with grays, browns, navies and even black clothing as we used as an example here. It’s that versatility, plus the suede texture and low profile aesthetic, that has made the Dark Olive Suede Captain our default pull for anything from smart casual dates, casual professional events, and rugged fall outfits.
And optics are backed up by quality construction: Thursday Boot Co. uses only Tier 1 USA hides to ensure top quality leather. Goodyear welt construction (the best way to attach the sole to the upper, period) ensures they’re both re-solable and virtually waterproof. Unlike a lot of other premium vintage-style dress boots, which use leather soles, Thursday boots utilize studded rubber outsoles – meaning they can actually be worn when there’s water on the ground. Pretty important in a boot, if you ask me.
Thursday boots are handcrafted with a full glove leather interior lining, EVA comfort strips, and cork-bed midsoles for a comfortable fit. Add free shipping and returns and the Thursday Boot Co. Captain is one of a handful of great options for an affordable, quality alternative to the premium standbys.
See how to wear them:
Red Wing Heritage 6″ Moc Toe
The Red Wing Heritage boot is aptly named: Red Wing has been in business since 1905 and the Heritage is part of an uninterrupted tradition of built-to-last boots stretching back to your great-grandfather’s era. Like many of it’s leather brethren, the Heritage features Goodyear welt construction, but it’s augmented by triple stitching for extra durability.
The moccasin toe and white sole make this a visually striking boot, and there’s a story behind the sole. When originally designed, Red Wing chose a lightweight crepe sole with minimal tread design to reduce the mud that would cling to a farmer’s boots. You might think the classic reddish leather wouldn’t be versatile, but they pair well with any shade of tan, brown, navy, olive, and black in the rest of your outfit. Your options are virtually limitless.
One drawback we’re aware of is that Red Wings are notorious for being hard soled, but with a $3 set of insoles from Rite Aid these are my most comfortable pair of Red Wings and have become a casual staple of my wardrobe since I first got them in 2010. Casual and rugged, the Heritage Moc Toe is the perfect cross between style and functionality.
Red Wing Iron Ranger
The Iron Ranger represents the standard bearer for the Red Wing archival work boot. It’s made in America and features the same Goodyear welt construction and top-quality threadwork of their other offerings. The sole of the Iron Ranger stands out, however. Its nitrile cork, a durable material that sheds water and oil. It won’t dry out and crack like a rubber sole, and is more durable than a leather sole.
Design details like a cap toe (originally added to provide more protection for miners) and a wide back strap give an almost western feel to the boot that pairs exceptionally well with dark denim. They’re close to the top range for what many guys would consider reasonable for off-the-rack boots, but the Iron Ranger is something that will last you in some capacity until your boot-wearing days are done.
Tecovas Cartwright Calfskin
Tecovas is a newcomer in the scheme of Western boots – the company launched in 2014, after all – but they’ve proven a popular choice for guys who want to try out the Western boots trend without overdoing it. Sure, they stock styles made from exotic leathers, but they’ve also done a mighty fine job crafting rugged yet straightforward, classic cowboy boots.
If you don’t know where to start, but want a change of pace from lace-up or Chelsea boots, consider the Cartwright. With its understated and traditional Western-style detailing and handsome Calf skin leather designed to break in nicely over time, these are boots that nod towards the “Wild West” without overdoing it. Better still is the fact that you can complete your look with a Western shirt from Tecovas and a durable trucker jacket – also from the Austin-based brand – while still snagging a pair of sub-$300 boots.
Thorogood Moc Toe
In the world of boots the Thorogood Moc Toe and the Red Wing Moc Toe are in a perpetual stare-down. Both made in the USA with wedge-style soles and Goodyear welts, both handsome devils, both hailing from frigid north midwest states.
So what makes them distinct? The first thing that jumps out at you is the price tag: they’re widely available for around $250, about $50 less than the Red Wings. It isn’t pocket change, but it’s a deal considering the build quality and heritage. Thorogood’s Moc Toe was first introduced in 1964 as the “Hike ’n Camp,” the official Boy Scout Boot and has been selling strong ever since.
Other features that set it apart are a removable dual-density shock absorption footbed and comfort cushion. They’re also available with a hardened safety toe. Perhaps more than any other boot in the category these are meant to be worked in.
However, while a great, comfortable boot with silky leather, their notable downfall is that they do run a bit hot and heavy on your feet. If price, workability, cold weather, or out-of-the-box cushion is your priority consider the Thorogoods; for warmer weather and comfort other than cushion, go for the Red Wings.
Wolverine 1000 Mile Boot
Founded in 1883, Wolverine has been making the 1000 Mile boot since the early decades of the 20th century – so named because the hardwearing horsehide leather was said to last a thousand miles of wear.
While we can’t independently verify specific mileage, the modern day revival of the 1000 Mile boot is built to last with a Goodyear Welt and stacked leather sole. Still made in Michigan, home of Wolverine’s original shoe and tanning factory, and now constructed of Chicago-made Horween Chromexcel Leather, the 1000 Mile helped launch the vintage service-boot style with the onset of the Americana fashion movement of the last decade.
The leather sole keeps with the original design and creates a sleek profile that allows these boots to be worn with jeans or dress pants. But make no mistake, leather soles are not great options if you’re planning to encounter precipitation. In that case, you’ll want to opt for the recent lug sole variant that comes with a Vibram lug forepart and heel – which will set you back $300, and alter the silhouette to a more rugged one like the Iron Ranger. The 1000 Mile is also available in moc toe and cap toe styles.
While the low profile leather sole original easily transitions between casual and dressy, it also loses that dresy capability as it ages and wears unless well-maintained. Unlike the casual Red Wing Moc Toe which, like a Schott leather jacket, just gets cooler the more beat up they are, beat up 1000 Mile boots look awesome casually, but lose that buttoned-up versatility. The well known leader of the throwback dress boot category, if you have the $300+ to drop, the 1000 Mile won’t let you down.
→ Read Primer’s in-depth guide to reviving a worn pair of 1000 Mile boots
Grant Stone Ottawa
Grant Stone ($380)
New compared to brands like Red Wing and Chippewa, who’ve been around for well over a hundred years, Grant Stone’s founders have been in the boot business in some capacity for just 30 years. Neophytes compared to the old-school giants.
Peer beneath the hood, however, and you have a boot crafted with a unique focus on getting the details right. Beyond the Goodyear welt construction, all Grant Stone boots feature vegetable-tanned leather, which utilizes raw materials from various plants, woods, barks, fruits and leaves for a Chromium free all-natural product.
While at the higher end of the price-point, the Ottawa is one of the more agile and refined boots we’ve seen – the moc toe tapers upward for a sleeker and less chunky profile. The supple, warm leather tones speak of quality and pair well with chinos, cords, or quality jeans. And is a more “budget” alternative to the…
The Alden Shop ($607)
Our most refined entry of the rugged styles also happens to be the most bank-breaking, but let me make the case in two words: Indiana Jones.
The Alden “Indy,” technically the model 405, is reputed to be the boot worn by Harrison Ford in the classic trilogy (the more recent effort need not be discussed). In fact, images of Alden 405s we’ve sought out online from real owners make the case better than any marketing copy: they look like the slouchy, world-weary boots Jones wore to uncover treasure, beat back baddies, and win the girl.
Because of their lower profile, soft toe, and flat sole, the 405s straddle the line between dress and work boot. Compared to Red Wing and Thorogood moc toes they have a more cultured, equestrian look than anything you’d see tromping around at the steel mill.
Alden’s Indy boots are crafted from top-shelf Horween chromexcel leather and break in for a lightweight all-day wear that’s appropriate with jeans, chinos or – if you’re doing it Indiana Jones style – a gray three piece suit for teaching your undergrad archaeology seminar.
Nisolo All-Weather Chelsea
On the surface, Nisolo’s laceless Chelsea Boots check all the right boxes in a great pair of boots – a sleek profile, rich leather colorways and the ability to be dressed up or dressed down. Shock-absorbing low profile rubber soles are a handy design detail for all-day comfort. And there’s even more than meets the eye, thanks to a water-resistant leather upper and removable memory foam insoles. Nisolo takes things a step further, offsetting carbon produced in the making of these boots – they’re 100 percent carbon-neutral.
If you’re not convinced that Western boots are a major trend right now, just take a look around the hippest neighborhood in your town (or take a trek to Austin, for instance). The best styles are actually sleek and sharp enough to wear more like dressy Chelsea boots than boots you’d wear out on the ranch with boot cut jeans. And if you’re going to fully embrace Western boots, why not go all-in with a pair from a heritage bootmaker like Lucchese?
The company’s been crafting rugged boots from the finest materials since the 1880s, hence the higher price points on pairs like the classic, relatively straightforward Lewis Boots. If you want cowboy boots that aren’t quite as flashy as pairs made from an exotic leather, the tan leather, ornate boot shaft and iconic Western toe detailing check off all the right boxes.
The Original L.L. Bean Boot
L.L. Bean ($149)
You might call the Bean Boots the original and best: Often imitated, never precisely duplicated, and famed for their functionality – and for the rate at which they tend to sell out year after year. If it’s a pair of hard-working fall and winter boots you seek, the kind you don’t have to worry about getting a bit wet in the snow and slush, there’s hardly a better pair than this classic set of New England winter boots.
The blend of a waterproof full-grain leather upper and a durable rubber bottom is as ingenious now as when these boots were first designed more than a century ago, and small details like contrast stitching and two-tone laces add a touch of visual interest. Whether worn with flannel-lined jeans or work pants, worn for work or play, your next winter boots should probably come from L.L. Bean.
Danner Mountain Light
Every guy’s rotation of the best boots deserves a little variety and plenty of utility, does it not? No matter how often or how little you actually get out of town and hit the trail, don’t sleep on the wearability of a set of tough-as-can-be (yet comfortable as heck!) hiking boots. Menswear styles these days are mixing up the high and the low – like wearing a more rugged henley with dressier cotton chinos, for instance – and your boots rotation can do the same.
The USA-made, investment-level Mountain Light is a Danner classic for a reason, using a comfortable yet traction-focused Vibram outsole and classic mountaineering touches like sharp red laces (set against eye-catching leather). A moisture-wicking liner provides all-day breathability, too – it’ll prove especially useful if you do decide to take on a day hike.
→ Wondering how to style these? Check out Live Action Getup: Fair Isle
Allen Edmonds Higgins Mill with Chromexcel Leather
Allen Edmonds ($475)
If you notice anything about our Primer-approved picks for the best men’s boots, it might be the idea that quality beats quantity time and time again. As in: Why buy multiple cheap boots when you could snag a super high-quality pair – yes, for a bit more cash – and then wear them for years? That’s the idea behind Allen Edmonds boots, which cut no corners in production or classic style points, from the use of Chromexcel leather (we call it “the good stuff”) to the USA-made production.
This is a no-fuss pair of boots inspired by vintage logging boots, with the ability to pair up with everything from olive chinos, a henley and a trucker jacket to dark denim and an Oxford shirt. The best part? The more you wear them – and the more you take care of them appropriately – the better they’ll get over time. Talk about serious bang for your buck.
Oakstreet Bootmakers Cap Top Trench Boot
Oakstreet Bootmakers ($488)
That oft-repeated phrase “They just don’t make ‘em like they used to”… well, that phrase doesn’t exactly apply to Oak Street Bootmakers. The Chicago-based brand is a favorite of ours at Primer, and certainly a brand worth knowing – and wearing, of course. The difference, naturally is all in the careful, intensive design and construction process, resulting in boots that should prove absurdly durable and yet made to mold to your feet the more you wear them.
Horween Chromexcel leather, arguably some of the best leather for fine boots, should prove supple and dependable. It helps that the black colorway and sleek cap toe design are a dressy yet still wearable addition to your collection. Rubber-studded soles from Dainite provide maximum grip from day to night, and the use of rawhide leather laces is another craftsmanship-focused touch.
Clarks Wallabees in Maple Suede
Cousin to the more everyday designed Clarks Desert Boots, the Wallabees are a moccasin boot made in a host of colors and leathers with the brand’s classic crepe rubber sole. While to some they may be reminiscent of Grandma shoes, the Wallabees have quite a history with tastemakers and badasses. The Wallabees first came on the scene in the 1960s. By the 1990s, acts like the Wu-tang Clan (who all proudly wore Wallabees and even rapped about them) and Oasis were frequent sporters. In the recent past, hitters like Drake, Lebron, Kanye, and “I am the Danger” Walter White have all built fits with the uniquely identifiable boot.
While not as versatile as a more traditionally modeled boot, Wallabees are perfect for casual and smart casual outfits in fall, especially for a guy who isn’t looking for the Americana / workwear aesthetic common to a lot of boots.
Perhaps you’ve heard of famed French boots brand Paraboot thanks to your favorite influencer or through the inimitable style of Tyler, the Creator, but one thing’s clear to us – trendy though these boots might be, the brand is here to stay. They’ve been making chunky footwear using groundbreaking technology for nearly 100 years, and the brand’s use of rubber in developing hard-wearing boots has been imitated ever since. With the recent revival of looser fits, Paraboot’s chunky moc toe line has become de rigueur for fashionable menswear lookbooks.
If you want to try out some seriously versatile boots with an impossibly comfortable sole and a striking, distinctive silhouette, consider the Mucy Boots. For starters, the design is strong enough to anchor everything from tan corduroys (in the fall and winter) to breezy linen trousers (in the spring and summer). They’re an investment, to be sure, but the kind of splurge that’s the right move if you want a touch of flair in your rotation of the best boots.
They’re quite close in silhouette to, say, the Clarks Wallabee, but they use design details like a stacked rubber sole and a clean, three-eyelet design that’s dressier (ever so slightly!) than the famed Wallabee Boots.
White’s Chore Boot
With the continued endurance of workwear as a major style trend over the last 25 years, it’s sometimes easy to forget the intended purpose of boots, especially tough lace-up boots like those made by White’s. That purpose? Getting down and dirty and getting down to, well, work. If that sounds like a pair of boots you’d like to have
on hand underfoot, then the famed Chore Boots from White’s should do the trick.
The brand makes boots for loggers and farmers, and they’ve got a handsome array of “lifestyle boots,” but the Chore Boots toe the line between both categories quite nicely. The water-resistant leather upper is highly useful in conditions of all sorts, while the padded collar aids in day-to-night comfort. The contrasting Vibram lug sole offers both traction and a dash of off-duty style, too. It’s just up to you to figure out how and when to wear them now.
Quoddy Capetown Trail Chukka
Remember how we said the best boots in your collection should provide plenty of options? You should feel free to incorporate a dash of fun into the mix, too – fun by way of throwback-oriented chukka boots that mash up a moccasin and a chukka all in the one. There’s just something about these boots that, to us, calls to mind fall camping trips and crunching leaves underfoot – perhaps it’s the fact that Quoddy makes these boots in Maine the old-fashioned way (meticulously with handmade touches).
The Vibram mini-lug outsole offers up a smooth ride and useful traction on and off the trail, while the tan leather plays nicely with cold-weather colors like navy, burgundy and olive. For under $300, you might not find a better pair of casual, USA-made boots, and that’s something we can get behind.
Rancourt & Co. Acadio Chukka Redux
Rancourt & Co. ($325)
What is it about the Northeast that lends itself to brands making some of the most rugged, essential men’s boots? Whether it’s the weather and the need for footwear that can stand up to it, or just a good old-fashioned focus on doing things with added care and attention to detail, Rancourt is another New England brand worthy of a spot on any list of hard-working boots.
The Acadia Chukka is another time-honored blend of two styles (the chukka and the moc), set atop a crepe wedge sole for both contrasting style and loads of comfortable bounceback to keep you light on your feet. Chestnut leather laces drive home the casual styling potential of this pair, which perfectly nails that “fall in Maine” vibe – perhaps your next getaway is on the horizon.
R.M. Williams Comfort Craftsman
R.M. Williams ($539)
When a brand focuses on perfecting a style for nearly a century, it’s probably worth your time to give that company a shot, particularly when the name of the game is footwear. R.M. Williams took its first step on the long road to perfecting the Chelsea boot back in 1932, and you might say they still haven’t cut any corners on the path to perfection. It’s lofty praise, but when your boots are crafted by 80 individuals by hand, it’s hard to top that focus on craftsmanship.
That’s why these boots are so aptly named, made from a single piece of pull-up leather and set atop a hard-wearing rubber sole. Front and back pull tabs provide a distinctive design touch, and the chisel square toe gives them a dressy-yet-ever-so-slightly rugged appeal.
Fly across the pond (virtually, at least) to discover the wonders of boots made in Britain since the 1860s. It’s that laser-sharp focus that’s made Grenson a staple in the world of footwear, albeit one that’s both pricey and yet distinctly worth the investment. The Grenson Brady Boot is a prime example of the idea that you get what you pay for, with specs that rank with the best of the best in your boot collection.
The Brady Boots use a taller-than-usual hiker design, rich calfskin leather and a commando rubber sole for plenty of grip on slippery city streets. Although they’re functional in terms of design, they’re also sharp enough to wear with wool trousers come fall and winter. If you feel like your footwear rotation could use a shot in the arm via some one-of–a-kind boots, you might as well invest in the very best – in a way that’s going to turn some heads come boot season.
Jodphur boots were historically worn for horse riding, of all pursuits, but they’ve evolved over time into a polished and seriously sharp style for today’s modern man. If you’re seeking a change of pace from lace-up wingtip dress boots or even Chelsea boots, consider the refined style of the Jodphur, with its distinctive side buckles and smooth, streamlined silhouette. Better still, consider a refined pair from Carmina, all the better to really amp up your collection of the best men’s boots.
This pair uses luxurious touches like calfskin lining and a brown Vegano leather exterior, set atop a Goodyear welt sole for long-lasting wearability. The overall effect is super clean and simple, with the potential to wear these boots with a navy suit, grey chinos or navy corduroys come prime boot season – you’ll want to dream up as many ways as possible to wear these stylish boots, though.
Crockett & Jones Tetbury
Crockett & Jones ($695)
When a footwear brand is approved by James Bond, you can be sure it’s one worth checking out – and a potentially drool-worthy brand, at that. Such is the case with famed British heritage footwear brand Crockett & Jones, famously worn by Daniel Craig as 007 in not one, not two, but the past three James Bond flicks. The Tetbury is perhaps most famously worn by the man himself in exotic locales like Shanghai and Turkey, but you can wear these iconic boots anywhere on the planet – especially in a “suited and booted” look.
The black wax calf leather is the ultimate in a dress boot design, with a clean, sleek toe box design and Dainite rubber soles for Bond-centric traction (even if you’re no secret agent). Think of these like an investment-level pair to channel, well, your inner Double-O.
Nicks Handmade Boots Overlander
Nicks Boots ($549)
Remember what we said about the intended purpose of boots? To really get down to business and get to work? That’s an adage Nicks Boots takes to heart, overbuilding its boots in an impressive manner to meet the demands of the toughest jobs and conditions out there. It helps that styles like the Overlander are as ready for the town as they are for the trail, though. When you want durable boots that perform well alongside canvas work pants and yet can also be styled with a pair of blue stretch jeans, this could become your go-to pair.
The key here is the eight-inch design, ready for work and ready for intense weather conditions, coupled with an intense Vibram lug sole and visually striking brown leather. Boots that can pass muster in situations meant for both work and play deserve a special place of honor in your closet, in our opinion.
We’re excited to partner with Thursday Boots on this post because they’re the perfect Primer boot brand. If their confidence in being listed with 23 of the other best boots on the market doesn’t convince you of their assurance that you’ll love their boots, the specs will: Full grain leather, Goodyear Welt construction, and a price tag that’s half the price of similar boots. The President is one of the only affordable alternatives with these kinds of features and at under $200 it’s a no-brainer.
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