- Each year, the dizzying lineup of fall boots grows ever larger, making the decision of decking out your feet just that much more difficult.
- The best fall boots are subjective to the wearer, but some of our favorite pairs come from Thursday Boot Co., Timberland, Clarks, Dr. Martens, Frye, and L.L. Bean.
Fall is here, and it's time to break out heavier footwear as we meander toward winter. Ditching your sandals may be good riddance or a bitter defeat for you, but Insider Reviews is here to help you find your fall footwear whether you're going for trendy avant-gardes, timeless classics, or something in between.
First, let's consider where these boots will be walking. Cobbled streets laden with mysterious mud, sludge, and slime? Go for rubber or PVC and leave those leather soles alone — you'll only trash them. The office for a big board meeting? Revisit said leather soles — you might not want to rock up in Doc Martens looking like you just stumbled out of the darkest, dingiest bar in the dirtiest, oldest part of town.
You'll also want to keep the temperature and weather in mind. Is fall a wet proposition where you live? If so, think about avoiding suede which will, more likely than not, end up looking pretty raggedy come December. A full-grain leather with a waterproofing solution or balmlike ScotchGuard or one of Dr. Martens' signature shoe polishes is always a good idea.
After fashion comes function and comfort, of course. A lace-free Chelsea boot might be the most accommodating boot of all fall options and you can pull them off in just about any setting. But then, maybe you don't like that distracting patch of synthetic nylon breaking up the beautiful, shiny, natural leather for which you've paid such a premium. In that case, maybe a zippered boot with a harness or a full lace-up is your best bet.
When it comes to the leather you choose, try to go with the highest quality you can afford. All leather will break up and crease over time, but cheaper leather boots will almost always crease more and break up sooner.
Whatever your taste, we've got a pair of fall boots to suit your style and need below.
Here are the best places to buy fall boots for men:
- Thursday Boot Company
- Frye Boots
- Red Wing
- Dr. Martens
- Other notable places to buy stylish boots for fall
- Check out our other men's style buying guides
Updated on 9/29/20 by Amir Ismael: Added in Red Wing Boots and Clarks, and included more details for Timberland. Currently testing styles from L.L.Bean and Blundstone.
Thursday Boot Company
Thursday Boot Co.'s boots are sleek enough for the office, but rugged enough to handle the snottiest of cold, wet weather.
Somewhere in the crux between metropolitan and cowboy, Thursday Boot Co.'s boots would not be out of place in any closet, from those of country-boy wranglers to city-slicking dandies and everyone in between.
Most of the brand's boots can either be dressed down with jeans or paired just as well with a pair of pleated khakis. The soles vary as much as the styles, so there's everything from delicate cork (which we wouldn't necessarily suggest wearing to trudge through winter) to hardy Goodyear Welts and Vibram outsoles. Same goes for the leather.
The Insider Reviews team reviewed Thursday Boot Co.'s line back in early 2017 when the company was just getting going, and sentiments around the office, I can safely report, have not changed. — Owen Burke
Pros: Good quality leather, tough outsole
Cons: Cheap insoles and laces
Timberland has been making sustainable footwear since long before it was an industry trend — and there are plenty of styles to choose from.
Let's face it, as positive as sustainability is for consumers and the environment alike, it's very clear that many brands are hopping on the environmentally-conscious train because it's an industry trend, rather than stemming from a true appreciation for the planet. Timberland, on the other hand, has been quietly producing sustainable footwear long before it was trendy, and now it's starting to toot its own horn.
In 2007, the brand launched the Original Earthkeeper Boot, which featured interior linings made from recycled plastic bottles and recycled rubber soles. While that has become standard protocol for almost all sustainable shoes made today, it had never been done before when Timberland introduced the shoe 12 years ago.
Today, Timberland's environmental responsibility efforts are more sophisticated than ever before. There are a handful of sustainable styles for men, ranging from the Original Earthkeeper Boot and the Garrison Field Hiker to the 100% recycled plastic EK+ Brooklyn sneakers and even organic cotton apparel.
In terms of sustainable fall boots, the Courma Guy Boot is by far my favorite style. Drawing inspiration from the iconic 6-inch Premium Boot (commonly referred to as constructs or 10061s), the Courma Guy has that unmistakable Timberland look with a rounded toe, durable rubber sole, and padded ankle collar. The brand also released fleece-lined pairs for added warmth that you can wear well into the winter.
The key updates include an overall lighter design, recycled plastic interior linings and laces, recycled rubber outsoles, ethically sourced leather uppers from Silver-rated tanneries, and stacked foam in the soles for added comfort and style. As a huge fan of Timberland's classic designs (I currently own at least 18 different pairs), I'm happy to say that this fresh and sustainable take on their classic fall boot didn't disappoint. — Amir Ismael
Pros: Sustainable, lightweight compared some of Timberland's classic boots, affordable, lots of styles available
Cons: None to speak of
Frye's boots will never go out of style because they are classic, high-quality, and made from durable leather.
There's hardly another boot out there that comes anywhere near as close as Frye does to speaking to the heart of Americana, and the wild westerner that is surely alive and well somewhere inside each and every one of us.
Frye has been making boots for a century and a half, staying true as glue to everything the company and its boots ever stood for. It's done custom work for everyone from Gene Autry to Carole King and Richard Nixon.
Still, the company hasn't shied away from modernizing, which comes welcome to those of us who wish we could rock fully ornate cowboy boots in the office, but just can't quite pull it off.
I have a pair of Sam Harness boots from Frye that I bought more than a decade ago. Everything on them has stayed perfectly intact, though heavy wear on cobbled streets for a few years put the hurt on them.
I went to a cobbler and got them redone for the better part of a Benjamin, but it was undoubtedly worth it for me. If that's all that most of a decade's worth of extensive and abusive wear and tear costs me to get these boots back up to snuff, that still, year over year, keeps my footwear expenses low.
Frye might not make the trendiest boots on the planet, but the boots sit atop a throne of timeless simplicity that no ephemeral fashion trend or season will ever usurp. — Owen Burke
Pros: Tough suede, no creasing, leather sole, subtly sleek and classic style
Cons: The company has taken most if not all production to Mexico and China, and skepticism is burgeoning over whether Frye boots will hold the same standard of quality going forward
Clarks has a wide array of timeless classics and new silhouettes for casual style and comfort.
Founded in 1825, Clarks is a nearly two-century-old brand — and that should say enough about its position in footwear. The UK-based brand is easily one of the best places to buy fall boots because it has choices for everyone. While styles like Wallabees and Desert Boots from the Originals line will appeal to people looking for timeless designs, the brand has collaborations and unique colorways down to a science.
If you're a sneakerhead, but really need something to wear other than your sneakers, Clarks probably has a pair you'll appreciate. They've teamed up with brands like A Bathing Ape, Bodega, Todd Snyder, and plenty of other cool companies. On top of that, they've got a wide array of fashion-forward colorways — not just your basic black, brown, and tan colors.
As a sneaker collector, Clarks has always been the natural choice for creating just as much variety in my boots collection as in my sneaker collection. The last time I counted, I had about 13 pairs of Clarks.
Beyond the variety, Clarks are great because they last an impressively long time. I got my first pair of Wallabees in 2009, and they're still in great shape today. The leather has held up well with basic care and the crepe soles have many more years of life left in them. Although I have a bunch of other pairs to wear, I won't be getting rid of my first pair until they're no longer wearable — and I've got a ways to go before that happens.
Pros: Has streetwear appeal, many colors and collaborations available, long lifespan
Cons: Not all styles are waterproof
Red Wing's iconic Moc Toe Boot is practically synonymous with the brand. It's durable as ever and timeless in style.
Red Wing Shoe Company was founded in Red Wing, Minnesota in 1905, but it wasn't until 1952 when its most iconic style, the Moc Toe Boot, was released.
The Red Wing Moc Toe Boot features a distinctive moc toe shape and a Traction Tred rubber outsole. While the style has been replicated by or been the source of inspiration for other shoemakers over the years, Red Wing's is the original.
The Moc Toe Boot was initially designed for hunters and other sportsmen, but became a dependable choice for farmers, construction workers, and anyone else who wants an extremely durable boot.
Today, Red Wing also has a work boot collection, leaving the Moc Toe Boot and other legacy designs in the Heritage collection. With that said, many of the Heritage pieces are still fully capable of handling work boot duties.
As with most boots, Red Wings run a bit large. I went a half-size down from my normal shoe size and I was able to comfortably fit a pair of thicker socks with some wiggle room. If I wanted to put on really thick wool socks, there wouldn't be an issue.
The only thing worth noting is that Red Wing's durability comes with a bit of a break-in period. The leather is on the stiff side and will take a few wears to loosen up. If you're looking for boots that are comfortable right out of the box, these may not be for you, but if you can stand to wear them a few times before they reach peak comfort, then go for it.
Pros: Durable leather upper, rugged outsoles, classic styling, lots of colors
Cons: Not much cushioning, takes time to break-in
Grenson Boots have been around since the 1860s, and they've clad the feet of British Armed Forces through not one but both world wars. These are not soft-soled boots.
If you're looking for boots that will handle a few thousand country miles but look good, and keep your feet dry all the while, Grenson is a heritage brand out of England that's been running the same factory for over 100 years.
William Green was just a kid when his mother taught him how to cobble a boot, and he simply took off running. Within about 15 years, he'd hired some of the best shoemakers in the business and built his own factory.
That factory, as it happened, turned out to be one of the first in the world to turn out a Goodyear-welted shoe, which is the most durable, but also among the easiest to replace because the welt makes a buffer between the insole and the outsole, so while it's sturdy, when it comes time to replace the outsoles (the uppers will last forever), it's an easy separation. Read more on welt construction here.
These boots are probably a little too rugged to pull off with a suit, but that doesn't mean they couldn't handle a vaguely formal affair. In our opinion, though, a good fall boot should be built to last.
Pros: Sturdy, classic, hand-painted
Cons: None to speak of, other than they might not be as dressy as the office (or a suit) requires
Bean Boots will serve you well through both fall and winter, and they go with most outfits.
L.L. Bean's Boots were introduced in 1912, and haven't changed much since. That's because they haven't had to.
Leon Leonwood Bean did anglers and hunters a serious solid by tacking together these remarkably warm and dry boots. The Bean Boots went onto become the genesis of his stardom over a century ago. Today, you'll find them everywhere from the backwoods of Maine to the boroughs of the Big Apple.
While many of L.L. Bean's products are being made offshore these days, the company continues to craft a select few of its products stateside, including the beloved Bean Boots.
Constructed using rubber bottoms and soles, a steel shank, full-grain leather uppers, and 3M Thinsulate, these boots have hardly changed since the start. Of course, there was no 3M nor Thinsulate in the early 20th century, but the design, the leather, and the rubber have all remained the same.
One thing that has changed L.L. Bean's boot game is variety: There are more than 30 styles of Bean Boots to choose from with an array of linings so there's a pair for each season.
These boots are part of the history of exploration and expedition themselves, having gone to war for the United States Army and forayed both poles. They are also storied to have found their way onto Ernest Hemingway's feet, who, according to GQ, even went so far as to recommend them himself.
Unfortunately, L.L. Bean's lifetime guarantee — not dissimilar to Dr. Martens — was discontinued this year, and purchases only come with a one-year warranty from here on out. We're sad to see this longstanding tradition go, but will still stand by Bean's boots unless the quality itself starts to drop.
Pros: Sturdy, high-end leather and rubber, steel shank for support, not outrageously priced, hand-stitched
Cons: Maybe not the most fashion-forward boots you'll come across this season (or next), but their beauty lies in their utilitarianism
Doc Martens are made with top-notch materials, handled with love, and rife with history.
Dr. Martens' AirWair is an emblematic piece of footwear synonymous with the predominant sub- and counter-cultures of every decade since their introduction in 1960: the skinheads in the '60s, the punk rockers in the '70s, the new wave artists of the '80s, and the grunge scene in the '90s. Today, they may be more ubiquitous than ever.
Doc Märtens' first endeavor in footwear came during his time serving as a doctor in the Alps during World War II. After having hurt his foot while skiing (presumably during R&R), he decided that the standard military-issued boots he'd been wearing just weren't sufficient enough for him to nurse his foot, so he thriftily cobbled together a pair of his own using softer leather and rubber from discarded tires. Back in Munich, Märtens bumped into an old friend who was intrigued by his innovation and the two teamed up, refining the design, adding the signature yellow stitching, and anglicizing Märtens' name.
Recent years have shown the company its fair share of hardships, and the brand briefly shuttered most of its production houses and stores in the UK in the early 2000s. The company seems to have bounced back in recent years, however, and in early 2018 Business Insider reported that Dr. Martens has been producing some 10 million pairs annually.
Dr. Martens' AirWairs are some of the most durable and versatile kicks around. Let's start with the air-cushioned soles. They're not glued but melted to the welts using hot blades and rollers so that as both components cool, they forge one single piece of inseparable PVC. if you don't believe me, watch this delightful Insider video to see just how well they're made. If the de facto black is a little too punk rock or goth for your taste, there's always cherry red, navy, green, and white.
Sadly, the company has discontinued its "for life" boots, which were about three times as expensive, a little sturdier (and heavier), and guaranteed — with free repairs — for life. The base model 1460s and 1490s are a more-than-reasonable middle-of-the-road boot well worth their price tag for anyone plying muck-ridden urban streets and sidewalks. Just be sure to pick up a tub of the Wonder Balsam to treat the leather (at least once) before you wear them. It's worth it.
Pros: Sole and welt are melted together and will never separate, affordable, waterproof, air-cushioned soles
Cons: The "For Life" boots are discontinued, and these soles will likely wear out after a few years (like many of not most boots in this price range)
Other notable places to buy stylish boots for fall
If you're really looking to be styling, there's scant a better place than Mr Porter to shop boots, where you'll find all the classics from Saint Laurent to Bottega Veneta and Tom Ford.
Splurging, when and where we can, is often worth it, which is exceptionally the case when it comes to footwear we want to last.
If you really want to knock your socks off, Mr Porter is where you'll find shearling-lined, polished-leather, whole-cut, and heaviest-weight Utah leathers from all the usual suspects in the designer department: Brunello Cucinelli, Loro Piana (where the immensely casual meets the definitively styled), Moncler (for over-the-top hiking boots), Berlutti (whose Venezia leather might make the most beautiful Chelsea boots on this earth), Tom Ford, Edward Green, and of course, Prada.
All these brands have their own legacy, and we'd be foolish to point you toward any single one of them. You, after all, know what you like, and just about every style imaginable can be found in Mr Porter's unbelievably and meticulously detailed inventory of men's boots, which for this fall season sits at around 120 different pairs.
From the utterly outrageous to the reigned-in and reserved, they're all there. Go wild.
Pros: A smartly curated selection of the best designer boots you can find
Cons: Well, do we even need to say? Apart from there being too many choices, cha-ching.
Check out our other men's style buying guides
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