- Fall boots are a perfect transitional shoe for when it's too cool for sneakers, but not cold enough for heavy-duty winter boots.
- Which boots you choose to wear has everything to do with where you plan to wear them.
- Some of our favorite pairs come from Thursday Boot Co., Timberland, Clarks, Dr. Martens, Frye, and L.L. Bean.
Although we typically assign boots to cooler temperatures, the truth is that fall boots are great for the transitional weather between winter and spring. They aren't as heavy-duty as winter boots are, but they still offer plenty of coverage for those in-between spring days when it could rain at any second. Fall boots also have the benefit of looking seriously slick. They can be dressed up or down, making them one of the more versatile pairs of shoes you can own.
With so many styles of fall boots out there, it's hard to nail down one pair that's the absolute best. So instead, we're pointing you in the direction of some of the brands making the best fall boots in 2021.
Here are the best places to buy fall boots for men in 2021:
Updated on 1/26/22: Removed Red Wing boots, as a system outage has caused low stock among retailers. We still stand behind the brand if you can find in-store, and will add them back into the guide once the stock increases.
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. The 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.
Timberland Courma Guy Boot
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.
Frye Boots
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. The brand 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. Luckily, a trip to the cobbler was all that was needed to have these boots looking brand new.
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.
Clarks
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. — Amir Ismael
Grenson
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.
L.L.Bean
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.
Dr. Martens
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.
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, thanks to 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 the de facto black is a little too punk rock or goth for your taste, there's always cherry red, navy, green, and white. Not a fan of the AirWair boots? The brand has a bunch of other styles that also rock.
Check out our other men's style buying guides
The best places to buy men's jeans
Jeans are personal, and buying them can be intimidating, but fear not, gentlemen. We're not here to hold your hand, but we will point you in the right direction.
The best men's undershirts
If you've been looking for the best undershirt for managing your sweaty pits, then the search is over. We've done the research and smoked out the best undershirts for men that you can buy today.
The best men's shorts
Finding the perfect pair of men's shorts can be challenging, so we've sorted through a bunch of options to find the best places to shop for men's shorts and selected our favorite pairs from each brand.
The best men's workout shirts
Ask any routine gym goer about their preferred workout attire, and they'll likely spend a few minutes talking about moisture-wicking fabric, innovative cooling technology, or sweat-activated fabrics. While these may sound like industry buzzwords, the application behind these concepts are staples — and, frankly, must-haves — in the world of workout apparel.
The best men's underwear
If there's one article of clothing that you ought to care about, it's your underwear. Our top pick is the Tommy John collection because you can choose from many different styles of underwear and all of them are seriously comfortable.
The best suits
For your go-to workhorse suit, you simply can't beat a single-breasted, two-button classic style charcoal gray suit.
The best ties
No suit is complete without a great necktie. For your staple tie, it's hard to beat a black silk tie.
The best white dress shirts for men
Every one needs at least one good white dress shirt. Here, you'll find the best of the best.