Despite popular opinion, the “most wonderful time of the year” is not the holiday season, it’s actually boot season. Boot season opens up at the beginning of fall and lasts until deep into spring, so we’re just getting started out here. While we recently welcomed back flannel, layering and our favorite pairs of jeans a few months back, we’ve been rocking boots ever since the weather dipped under 60 degrees. There’s just no feeling better than opening up, smelling (trust us on this) and slipping on of a new pair of leather boots to celebrate the changing season.
The best men’s boots can hold the weight of being the centerpiece of your cold-weather wardrobe. They turn good outfits into great outfits and, if styled well, can make you look really smartistic (smart + artistic; credit: me, who is wearing boots right now). But the truth is that boots know no boundaries, and every unique type of style has at least one boot to match. Seasoned boot wearers may be keen on the ins and outs of what looks good, but for newbies, finding a good pair of boots can be very overwhelming.
Here’s how to start shopping for your next pair.
Types of Men’s Boots Out There
Most boots were designed with blue-collar workers and laborers in mind who needed rugged performance footwear to withstand the demands of their jobs. A handful of American brands still make their boots to these original specifications and, in some cases, use the same exact production methods they did nearly a century ago. This just proves that quality goods matter.
Today, you’ll find stylish boots that can be worn either for function or fashion, for sometimes both, with most incorporating technology and materials to boost performance. In many cases, you’ll stumble upon boots that work well both dressed up or down, but it’s important to know what type of boot you’re dealing with in order to choose the best pair for you.
Let’s break it down:
- Cap Toe: A cap toe boot has an added piece of leather covering a toe, i.e., a cap, typically with a stitch across the toes. These can be dressy and/or casual.
- Chelsea: Unofficially named after the Chelsea area of London, Chelsea boots are a pull-on style that uses goring, or elastic fabric, on the sides to easily insert your foot. These can be dressy and/or casual.
- Chukka: Created by footwear brand, Clarks, a chukka boot sits right at or above the ankle with open lacing and only two to three eyelets. Clarks’s original release was what’s called a “desert boot,” because of its ties to Burma during WWII. These can be dressy but more often than not they’re worn casually.
- Moc Toe: A moc toe boot has a raised, stitched, U-shape seam that curves over the toes and extends back toward the ankle. This style was inspired by traditional moccasins. These are typically a casual boot.
- Outdoor: Outdoor boots are made with the sole (pun intended) purpose of withstanding and protecting you from elements. Outdoor boots include snow boots, hiking boots, duck boots, welly boots, and more. Casual, for sure.
- Riding: Riding boots were originally designed for the purpose of riding horses, so they’re built tall to protect the rider’s legs and with a block heel to better grip a stirrup. This category has evolved in modern times to include riding motorcycles. Modern moto boots are worn casually. Another popular variation of a riding boot is the much shorter shafted Jodhpur boot, which can be worn dressed up or casually.
- Wingtip: Similar to the cap toe and the shoe style of the same name, a wingtip boot features a winged broguing on the toe and down the sides of the boot. These are typically very dressy.
The best boots this fall are a combination of legendary styles we know and love, current trends, and rising stars you definitely need to know about. There’s a lot to consider here, but we’ve compiled 25 of the best men’s boots right here in our Ultimate Guide to Boots for your convenience.
1. Cole Haan ZERØGRAND Hiker Boot
Technically speaking, it’s not our exact pick for the best boot of the 2020 SPY Man Awards, but it comes pretty dang close. This past fall, Cole Haan released its upgraded 4.ZERØGRAND boot, which was easily the best men’s boot to drop last fall. It had a rugged yet modern look that was made for both the streets and the trails. Sadly, the boot was so damn popular, it’s completely sold out right now. For now, check out the 4.ZERØGRAND’s little brother, the ZERØGRAND Hiker.
It has *almost* everything the 4.ZERØGRAND does, but it’s slightly outdated. Nonetheless, it’s an incredibly handsome pick we’re totally in love with for winter.
SPY MAN AWARD WINNER
2. Dr. Martens 1460
LARGEST CULT FOLLOWING
Like the Clarks Desert Boot, you’ll know Dr. Martens’ 1460 as soon as you see it. This boot is easily recognized by the translucent Dr. Martens air-cushioned sole and iconic yellow welt stitching. The 1460, which was officially released on the first day (1) of April (4) in 1960 (60), was originally sold as the go-to work-wear shoe for postmen and factory workers. It didn’t take long before the style was adopted by the rebels of Britain’s underground music scene, including the infamous Pete Townshend of The Who.
Since then, the Dr. Marten 1460 has become an international symbol of individualism, going against the grain of society, and most certainly, comfort. You can find the 1460 in just about any color imaginable, but the most popular will always be black. Style your Doc’s with anything you feel like putting on, because these boots mean not giving a flying f*** about what society, your mom or anyone else thinks about your clothes. Do wear socks, though — trust me.
3. Timberland 6” Premium Waterproof Boot
BEST FOR RUGGED STYLE
This boot may be one of the most iconic in modern times. The Timberland 6” Premium Waterproof Boot was originally designed to handle the unforgiving New England terrain and weather that construction workers had to regularly endure. And it worked! Since 1973, the boot’s waterproof, seam-sealed Horween leather design has blocked out splashing from puddles or rain while the durable rubber outsole has provided as much offense on the ground as it does defense for the foot inside it.
What Timberland didn’t see coming was the massive impact this style would have on hip-hop culture a couple of decades later. The ’90s saw legendary artists like The Notorious B.I.G and Tupac Shakur. Today, the Timberland 6” Boot has been spotted on the likes of Rhianna, Kanye West and athletes by the hundreds. Wear this staple boot with your favorite jeans, whether loose or skinny and a plaid flannel shirt or jacket this fall.
4. Converse Chuck 70 Bosey GORE-TEX
BEST FROM CONVERSE
Don’t be so shocked to find out your favorite shoe brand for as long as you can remember makes boots. Made from a water-repellent canvas, the Chuck 70 Bosey GORE-TEX boots take your classic Converse to a whole new level but still keeps it as rooted as ever. You know you want to wear Converse in the winter anyway, so this is exactly how you can until you can rock your Chucks again in the spring.
Wear these with your regular street style. Hell, even bring them on the trail. You do you!
5. L.L. Bean Boots
BEST DUCK BOOT
Made in Maine for over an astounding 100 years (since 1912), theL.L. Bean Boot is a New England, and arguably an American, staple for all-terrain and all-weather footwear. Described as the “antidote to wet feet,” this boot combines a full leather upper with a completely waterproof rubber sole that boasts some of the best damn traction you’ve ever seen. The “Bean Boot,” designed by L.L. himself in 1911, was originally used for hunting but has taken on a much more broad role over the years. Many living in the northeast wear these during the wet months to protect themselves from harsh weather, with some having worn the style since childhood. The Bean Boot is also commonly found as the boot of choice on college campuses! Wear this boot in the fall with a tough pair of jeans and a quilted wool or nylon puffer jacket, maybe from Barbour.
6. Blundstone 500 Chelsea Boot
BEST CASUAL CHELSEA BOOT
Chelsea boots are a do-it-all kind of boot. Surprisingly, not many brands are actually well-known in mainstream American shoe culture for making a Chelsea boot. Blundstone, boasting over 150 in the footwear game, takes exception to that with the original 500 series. Blundstone’s 500 Chelsea Boot hails from the 1960s and was originally used, like many others listed here, by farmers and other blue-collar workers.
7. Clarks Desert Boot
BEST DESERT BOOT
The Clarks Desert boot is not only the most iconic chukka boot, but it completely rocked British and American boot culture back in 1950. Nathan Clark created his famous desert boot after drawing inspiration from the boots off-duty worn by army officers while stationed in Cairo and Burma through World War II. The Clarks desert boot is a staple casual boot and is distinctly identified by its crepe sole, made from coagulated latex. If you’ve never felt a crepe sole, imagine what it would feel like to touch mashed potatoes after covering them with a full can of hairspray — it’s different.
Today, this boot is made from the exact same measurements and materials as the first one made by Nathan Clark, himself. Wear this with a cool crew sock, something with texture and do it justice by cuffing up the bottom of your pants or wearing a pair of joggers. If you’re a daring lad, try wearing them with long socks and shorts!
8. UGG Freamon Weather Chukka
BEST SNEAKER SOLE BOOT
We’ve mentioned winter weather a few times so far. If you’re not into heavy-duty utility boots, here’s one for you to consider. The UGG Freamon Boot has been around for a handful of years now and has steadily become a staple in the shoe lineup of modern men everywhere. This chukka boot is constructed with a waterproof suede upper, a lightweight foam sole and a supportive, antimicrobial, leather-lined insole for wearing with or without socks. These boots are insanely flexible and look great as a casual chukka or even with business-casual outfits. Use the Freamon boot for walking around town to stay comfortably agile and light on your feet.
9. Frye Harness 12R
BEST FOR RIDING THINGS
That’s right, best for riding things. Here’s the story. New England neighbor to L.L. Bean, the Frye Boot Company dates back to 1860’s Massachusetts. Their boots were worn by soldiers on both sides of the Civil War and by the American cavalry during the Spanish-American War, including a young Teddy Roosevelt and the Rough Riders. Flash forward to the 1970s, the Frye Harness 12R boot was released as a tribute to these military riding boots and given a detailed upgrade with the metal ring harness around the ankle. While most people in the ’70s weren’t on horseback, motorcycle culture adopted these as the go-to boot to keep them safe. In fact, one review on the company’s website even says their boot saved them from being severely injured in a minor crash. Whether riding horses or a motorcycle, these boots go best with denim and other leather garments. Try it with black jeans and a thick leather jacket, maybe from Schott NY.
10. Thursday Boots Legend Chelsea Boots
BEST OFFICE BOOT
Back in the office? Whether you are or aren’t, these are the boots to have on when strutting from your desk to the bathroom. The matte black color is a subtle flex that keeps you in both the foreground and background at the exact same time when having them on, which is exactly what you want in terms of office wear. They don’t cost nearly as much as you might think, either, which is great for your bank account. We loved them so much, we named them a favorite in our 2020 SPY Man Awards.
Pair these with just about anything you wear to work. With these, you will look good no matter what.
SPY MAN AWARD WINNER
11. Wolverine 1000 Mile Boot
BEST WORK BOOT
We raved about this boot in a previous article, but Wolverine’s 1000 Mile Boot is the real deal. Described by Wolverine as “America’s Original Workboot,” the 1000 Mile Boot of today is a recreation of the original design from 1914 that sought to provide both comfort and toughness to the grueling daily life of the average working man. This boot is still 100% produced in the United States.
The leather upper is made from Chicago-produced Horween Leather, the classic leather sole and Vibram rubber heel from Williamsport, Pennsylvania and the flat waxed cotton laces are made in Landrum, South Carolina. The most popular color in this boot is brown, but many colors are available today. Choose your pair wisely, because chances are they’ll outlive you.
12. Red Wing 6” Moc Toe
BEST MOC TOE BOOT
Red Wing’s 6” Moc Toe boot is the most iconic moc toe boot for men. Released in the 1950s, this moc toe boot was originally designed for sportsmen but quickly became a favorite amongst blue-collar workers in factories and on farms. For 70 years, this boot has provided the same exact durability, traction and all-day comfort through high-quality leathers and excellent design. Aside from the moc toe, this boot is easily recognizable thanks to its chunky Traction Tred rubber sole.
Today, the Red Wing 6” Moc Toe boot has become one of the most popular lifestyle boots. They’re basically attached to the feet of “denim heads,” or people who have a denim-first wardrobe because the sturdy leather is a perfect compliment to raw, rigid denim. The best type of look for this boot is that pseudo-lumberjack vibe with a pair of cuffed-up slim fit jeans, a clean white t-shirt, and a denim jacket. Note: Order a half to a full size down.
13. UGG Butte Waterproof Boot
Kiss cold tootsies goodbye with the best boots for dudes with chronically chilly feet. If you find yourself doubling or even tripling up on socks, stop it. Just buy these waterproof UGGs and call it a winter. Each pair is waterproof and made with a faux fur called UGGpure, which is made entirely from wool but feels and wears like genuine shearling.
Throw these on before you have to head outside and shovel snow. Your feet are going thank you.
14. Saint Laurent Wyatt 40 Zip Boot
SHARPEST DESIGNER BOOT
The Saint Laurent Wyatt 40 Zip Boot is just pure sex appeal for guys who know how to WALK-THAT-WALK. This boot has been a revelation for the Saint Laurent man, providing him with a do-all boot for dressing up. This version of the Wyatt, which comes in more than a handful of variations, goes on easily thanks to the inside zipper and includes the 40 mm block heel to nail first impressions by making a clear statement. These boots feel couture AF once you’re inside them. To do these boots the justice they deserve, throw on a midnight blue, shawl collar tuxedo jacket with a pair of slim or wide leg jet black tuxedo pants, shirt optional.
15. Beckett Simonon Dowler Boot
MOST VERSATILE BOOT
Most people would like to pay a fraction of the price for quality goods if they can. Beckett Simonon is one of a handful of new brands that are making that happen in the shoe department. The Dowler boot from Beckett Simonon was previously ranked as one of the best dress shoes for men by SPY because of their attention to detail, use of high-quality materials and incredible versatility when styling an outfit. They’re able to pack all those into a pair of incredible boots at a lower, mid-tier price of $229.
It seems too good to be true but it’s really just better company operations passing on the savings to us, the customer. These boots rock, I have a pair myself. Get the Bordeaux color, you’ll be glad you did, and wear them both casually with jeans or dressed up in your autumnal wool suits.
16. Yuketen Maine Guide DB Boot
Paisley isn’t something you’d necessarily expect to see on a pair of winter boots, is it? Low and behold, the boots you never thought existed: the Yuketen Maine Guide DB boots. Featuring white paisley all over a navy exterior, you can pair these with a more monotone outfit for a subtle pop. The pair has a high-quality sole so they’re not going to give you any problems or break mid-walk. They aren’t necessarily made for hikes but will look excellent on a weekend escapade to the city with your pals.
17. Thursday Captain Lace Up Boot
BEST FIRST BOOT
If you haven’t been able to tell so far, there is a very large sea of boots to try. How is one supposed to even start scouting their next pair? Over the last eight years, Thursday Boot Co. has gained a massive following for its take on classic styles at very affordable prices. Thursday’s Captain boot, seen here, is a modern take on the classic factory work boot. The Captain, shown in Terracotta, is made with a full-grain leather upper, Goodyear welt construction and numerous types of padding and shock absorbency for comfort. All of this is mounted on top of a durable, studded rubber sole for great traction.
Whether you’re a boot connoisseur or are beginning to scout for your first pair, the Captain is one of the best men’s boots for anybody to wear. Choose from 14 different colors and leather types and also wide widths available. After you fall in love with these boots, take a look at their leather jackets!
18. TAFT Jack Boot
BEST MINIMALIST BOOT
TAFT may be one of the hottest footwear brands born online as of late. With a cult following, TAFT has popped up as one of the new leading faces in the world of boots, but also sneakers and dress shoes. The TAFT Jack Boot, in particular, is one of the styles that put the brand on the map. It’s the perfect combination of minimal and interesting while providing a near-perfect flex player between dressing up and dressing down an outfit. The use of raw wool for the upper with a sturdy leather cap toe and heel counter are the king of compliments when it’s on foot. With more than a whopping 1,100 reviews and a consistent five-star rating, you know this has to be one of the best men’s boots for fall. Grab it in your favorite color-way, including navy with brown, grey with black, plaid with brown, among other options.
19. Grand Voyage Bowie Mid Boot
BEST BOHO STYLE BOOT
This boot rocks; it’s in the name! The Grand Voyage Bowie Mid is the perfect boot for men’s boho style. Just like David Bowie, the silhouette is somewhat fluid. It looks exactly like a classic jodhpur boot, buckle and all, but has an inside zip for easier access. Handmade in Italy, you can look forward to a soft, full-grain upper on a leather stitch sole with a memory foam insole for added comfort on top of an elevated block heel. It looks best with skinny jeans and works with pants tucked in and also out and over the boot.
To really hit a home run with this boot, wear some distressed black denim and find yourself a good medium to wide-brim hat in black, beige or a neutral green.
20. Ankari Floruss Wednesday Chelsea Boot
MOST VERSATILE CHELSEA BOOT
A refined, black leather Chelsea boot is a cornerstone of the modern man’s shoe collection. If you want to wear it with a pair of jeans, a tee and a flannel or jacket, it looks super smart. If you want to wear it with a blue suit, it also looks super smart. In my opinion, Ankari Floruss, a relative newcomer to the shoe world, is one of the better options for this type of boot. The Wednesday Chelsea Boot from their “Seven Days” collection is full-grain leather throughout and handcrafted in Italy. One of the loudest gripes about Chelsea boots is that the circumference of the opening is too wide for the leg inside it, but this boot’s measurements are spot-on. If you’re not into black leather, the dark brown suede version of this boot is also incredible.
21. Ariat Rambler Boot
BEST COWBOY BOOT
Cowboy boots are having a moment in the fashion world. This makes sense, seeing as how most of the boots in the Legendary category stemmed from workwear. The Rambler boot from Ariat is the single best selling cowboy boot on both Zappos and Ariat’s online store, and seemingly for good reason. Ariat describes this boot as “bare bones and broken in” in order to “Nashville to L.A. and Austin to Boulder.”
The Rambler is the do-all western boot for guys, and that can also include just looking great and feeling great, thanks to the cushioned insole, on a day-to-day basis. If you’re new to the western look, the Rambler boot shaft is an ideal height for all guys and perfect for tucking in pants or otherwise. Match it back with any wash of blue slim or bootcut denim, a trusty ol’ white t-shirt and a lightweight button up. Bonus points if it’s a dual chest pocket western button up.
22. TAFT Viking Boot
James from SPY’s editorial team here. Though I didn’t have to, I felt it necessary to add TAFT’s latest, the Viking Boot, to this round-up. Why? Well, because it’s a boot every guy should be aware of. Look, I have a solid boot lineup — including a couple on this list — but none are as comfortable as the Viking Boot. TAFT was kind enough to send me a pair to try and immediately after slipping my foot inside, I understood the hype. The Vibram sole is the stuff of dreams and will encourage you to go for a stroll right then and there.
But it’s not just comfort with this one, no sir. Even from a distance, you can’t help but marvel at the beautiful detailing. I had never seen pebbled leather on a boot before but damn does it look good IRL. From the brass eyelets to the leather trim, this is a boot that feels well thought out. And it is.
But don’t take my word for it. TAFT’s site shows hundreds of five-star reviews from extremely stoked customers. If you’re in the market for a boot that is durable and stylish, you can go ahead and stop your search with the Viking.
23. Merrell Moab Mid 2 Waterproof Boot
BEST HIKING BOOT
With many gyms still closed after months of COVID-related issues, outdoor exercise has become more prevalent than ever. Hiking as exercise is awesome, especially when surrounded by the beauty of nature in fall. But it’s important to hike in the proper footwear. The Merrell Moab Mid 2 hiking boot is part of the “Mother of All Boots” collection, which is an accurate descriptor for this do-it-all boot. This waterproof version of the Moab 2 boot is perfect for the uncertain outdoor conditions that fall may bring in certain regions of the country. In other words, it keeps you on your toes when treading terrain turns treacherous.
Whether your trail crosses water, scrambles across ridges or simply requires a boot defensive enough to unwaveringly step on rocks, this technically-designed boot can handle it. If you go with this as your hiking boot, you’ll find solace in the ample ankle padding and support.
24. Bed Stu Protege Boot
BEST DISTRESSED BOOT
Bed Stu is a brand that has always paid attention to detail and then taken their designs a step further. The Bed Stu Protege boot is an artistic play on the classic blue-collar work boot but designed for the sake of style. The Protege’s handsome vintage-finished leather upper is done with a chrome-free vegetable tanning process by real people in Leon, Mexico. The Goodyear welted sole also allows this boot to be resoled after it wears down, but that doesn’t happen easily. Personally, I’ve worn Bed Stu footwear for a few years and can confidently say their shoes are some of the most compliment-worthy I own.
Rock these distressed boots with a faded black pair of jeans and your favorite shirt jacket. Roll the sleeves up and a wide-brim hat to complete the fall look.
25. Hunter Original Short Rain Boots
BEST RAIN BOOTS
Live out your rubber ducky fantasy with the rain boots of all rain boots. These are the epitome of what you imagined each and every rain boot looked like as a child. There really is something super iconic about the bright yellow staple making its way out in fashion by trudging around in the rain. Get a pair for yourself, you’re well overdue.