The Ultimate Guide to Men’s Boots in 2020: Icons, On-Trend and Must Know’s

Image courtesy of Taft
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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, while we also welcome back flannel, layering and our favorite pairs of jeans. That’s all great, but there’s no feeling better than opening up, smelling (trust me on this) and slipping on 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 fall 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 to 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.




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 21 of the best men’s boots right here in our Ultimate Guide to Boots for your convenience.




1. Clarks 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!

a pair of Clarks Desert Boots Image courtesy of Zappos

2. Dr. Martens 1460


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.

Dr. Martens 1460 Image courtesy of Zappos


3. Timberland 6” Premium Waterproof Boot


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 the Timberland didn’t see coming was the massive impact this style would have on hip-hop culture a couple of decades later. The 90’s 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.

Timberland-6-Inch-Premium-Waterproof-Boot Image courtesy of Zappos

4. Red Wing 6” Moc Toe


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.

Red-Wing-Heritage-622-Moc-Toe Image courtesy of Zappos

5. L.L. Bean Boots


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.

8-Inch-L.L.-Bean-Boots Image courtesy of L.L. Bean

6. Frye Harness 12R


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.

Frye-Harness-12R Image courtesy of The Frye Boot Co.

7. Wolverine 1000 Mile 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.

Wolverine-1000-Mile-Boot Image courtesy of Zappos

8. Blundstone 500 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.

Blundstone-BL500 Image courtesy of Zappos

On-Trend Boots for Men


9. Saint Laurent Wyatt 40 Zip 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.

Saint-Laurent-Wyatt-40-Zip-Boot-1 Image courtesy of Farfetch

10. Beckett Simonon Dowler 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.

Beckett-SImonon-Dowler-Boot Image courtesy of Beckett Simonon

11. Taft Jack 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.

Taft Jack Boot Image courtesy of Taft

12. Grand Voyage Bowie Mid 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.

Grand-Voyage-Bowie-Mid-Boot Front Image courtesy of Grand Voyage

13. UGG Freamon Weather Chukka


We’ve mentioned fall 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.

UGG-Freamon-Weather-Chukka Image courtesy of Zappos

14. Ankari Floruss Wednesday 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 charcoal 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.

Ankari-Floruss-Wednesday-Chelsea-Boot Image courtesy of Ankari Floruss

15. Thursday Captain Lace Up 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 different 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!

Thursday-Captain-Lace-Up-Boot Image courtesy of Thursday Boot Co.

16. Ariat Rambler 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.

Ariat-Rambler-Boot Image courtesy of Ariat

Must-Know Men’s Boots for Fall


17. Merrell Moab Mid 2 Waterproof 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.

Merrell-Moab-Mid-2-Waterproof-Boot Image courtesy of Zappos

18. Stacy Adams Finnegan Wingtip Lace-Up Boot


This is one of the best men’s boots to drop this fall. This wingtip lace-up boot from Stacy Adams is doing it all with smooth, tumbled and suede leather as well as waxed canvas. The contrasting and complimenting tones also add depth to this boot to really make it pop. Add the memory foam insole for comfort and you’ve got yourself a pretty dope walking around boot. When you wear this, make sure you opt for a crop pant or just cuff up to show the true masterpiece that this is. For that dude who has tough-to-fit feet, this boot also comes in a wide. Rejoice!

Stacy-Adams-Finnegan-Boot Image courtesy of Stacy Adams

19. Bed Stu Protege 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.

Bed-Stu-Protege-Boot Image courtesy of Zappos

20. Taft Grail Boot


These are boots for the bold. Taft may be the king of the minimal boot, but they also take shots at decorative boots as well. The Grail boot, new for the season, is a full brogue lace-up boot with a brass-coated chain feature on the toe cap that’s handmade in Spain. This absolutely screams “couture,” but in a sophisticated, refined way; not the outlandish way you normally see on the runway.

For the guy who likes to stand out, this is the boot for you this fall. Wear this with your sharpest grey trousers and a double-breasted waistcoat to hit that vintage vibe or try a pair of dark, waxed skinny jeans, an oversized sweater and a wool fedora to find that modern sleek fit.

Taft Grail Boot Image courtesy of Taft

21. Blondo Konor Waterproof Chukka Boot


We’ve mentioned a few great boots to counteract fall weather so far, but none which qualify as a decent dress boot. Blondo is one of the few brands out there that specialize in dressed-up waterproof footwear. The Konor Waterproof Chukka boot is a clean, classic chukka silhouette made with a waterproof suede upper and rubber sole for good traction. This is the kind of boot you want to wear if you’re a city commuter who has to walk over concrete, grass, cobblestone and other surfaces when it rains or snows. The boot is also insulated to regulate heat when the temperature drops.

Wear this with your normal work attire during the week. On the weekend, definitely take it for a ride with a pair of jeans and a shawl-neck cardigan sweater.

Blondo-Konor-Waterproof-Chukka-Boot Image courtesy of Blondo

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