Originally designed for functionality, boots wore worn by men years ago only if their jobs depended on it. But thanks to serious developments and advances in boot construction, as well as the popularity of boots made famous by rock stars and celebrities around the world, it’s hard to really consider your shoe collection complete without at least a few boots in there. A great pair of boots can really elevate some basic pieces and take your look up a notch.
It can be hard to really know the difference between the dozens of different boot styles that are available, which is why we put this guide together. You’ll not only discover the difference between a Chelsea and a Chukka, but you’ll also find the top 3 picks in each boot category, selected for quality, design, and of course overall sex appeal.
Check out the 30 Best Boots You Can Buy Online Today…
Best Chelsea Boots
Back in mid-1800s England, the Chelsea boot was born. Until recently, you typically wouldn’t find this style of boot outside of the UK, but ever since the mod scene of the 1960s popularized these elasticized wonders, Chelsea boots have experienced a revival (thanks, Fab Four). With a slim silhouette, heel pull-tabs, and the ever-popular elastic side panels, the Chelsea boot is here to stay.
Pick #1: Blundstone BL 550
Even though this boot hails from an Australian lineage, its one of the best Chelsea boots you can find at a great value. The tough leather, classic design, and shock-absorptive construction makes it ideal no matter what industry you work in.
Pick #2: Unmarked French Toe Chelsea Boot
Handcrafted in Leon, Mexico (recently regarded as one of the shoe capitals of the world), the French Toe Chelsea Boots from Unmarked are highly regarded. The upper part features a smooth “mysterious” black cowhide from Mexico while the lining, insole, midsole, and outsole incorporate vegetable-tanned leather. Solid elements include brass nails, wooden pegs, and Goodyear welt.
Pick #3: R.M. Williams’ Craftsman Boot
In this best-selling boot, you can feel like an Aussie braving the wilds of the outback with this durable, hard-working boot. The Goodyear-welted construction makes it last beyond its expectations, while the single, one-pieced leather upper feels supple and sophisticated. If it’s good enough for the cowboys, it’s good enough for you.
Best Ankle Boots
Since ankle boots are often thought of as some of the coolest boots available, it puts the pressure on manufacturers to pull it off. Ankle boots have been made famous by rock stars and celebrities everywhere (often accompanied by tight pants and other classic wardrobe choices). Even though an ankle boot has a similar silhouette as a Chelsea boot, a true ankle boot will feature plenty of straps and zippers instead of elastic panels, which in many ways makes the ankle fit a lot more secure.
Pick #1: Rogue Boots by Thursday
Overall, we tend to love Thursday Boots because of their balanced combination of value, quality, and durability. We love their weather-resistant leather uppers along with solid Goodyear-welt cork beds that provide great comfort. The Rogue Boot is no exception, and it’s probably their most stylish design thanks to the outstanding Cuban heel that accentuates a noticeable Jodhpur artistry.
Pick #2: Saint Laurent Wyatt 30 Jodphur Boots
If you’re looking for sexy boots, you can never go wrong with Saint Laurent’s Wyatt 30 Jodhpur boot. With a striking upper suede and full-leather sides, this slick design and rock star appeal will shine through no matter where you are.
Pick #3: SSense Marsell’s Tozzi Boots
Thanks to its avante–garde style, these boots have a borderline fanatic following. Tozzi Boots have long been regarded for their craftsmanship blended with a unique design that is surely eye-catching. Made in Italy and featuring a special Blake stitch construction, we love little details like the fact that the grained calfskin uppers have been colored by hand, accentuated by what we feel is an insane amount of stacked leather at proportions that feel extreme.
Best Wingtip Boots
Some guys swear by their wingtip shoes, because they like the brogued details that provide a bit of formal touch to casual footwear. The versatility means you can go laid back and wear wingtips with jeans or cords, or you can fit them with your nicest suit. Wingtip boots are no exception, and here are the 3 best that you can get, no matter the occasion.
Pick #1: Velasca Sciostree Boots
Based in Milan, Italy, Velasca is known around the world for producing high-quality footwear at affordable prices. Their Sciostree Wingtip boots fit this profile, thanks to its tough Vibram lug sole that reminds you of shoes you’d find in the English countryside, combined with a leather upper that’s made of pebble grain kudu and highlighted by classic brogue embellishments.
Pick #2: Grenson Fred Leather Brogue Boots
Thanks to a chunky rubber lug sole combined with a water-resistant storm welt, you’re ready to take on the countryside with this solid English brogue boots. Its classy look comes from a well burnished yet subtle full-grain leather upper that can easily go with jeans or a full suit.
Pick #3: Thom Brown Classic Wingtip Boots
Often seen as a staple in any collection, American designer Thom Browne does it again with these well-made wingtips that feature a pebble grain leather upper, founded on a rubber sole that is accentuated by a shortwing semi-brogue design. We’re definitely fans of its iconic red, white, and blue stripe theme that extends to the grosgrain heel tab.
Best Chukka Boots
Also commonly known as the desert boot, the chukka first came around when fitted for WW II British soldiers who were stationed in Africa. These casual, all-leather boots eventually made their way up to the continent and over to the U.S., where they gained in popularity during the late 1900s because of their stylish look and feel combined with comfort and breathability that made them a perfect fit for hot weather. Although Clarks is probably best known for making the chukka boot famous, we’ve found other versions that you’ll like a bit more.
Pick #1: J Crew Unisex 1990 McAllister Boot
If you like boots made by mainstream producer Clarks, you’re going to love J. Crew’s version of the Chukka boot. Featuring premium Italian suede uppers combined with rubber soles with natural crepe, this boot feels more refined and better suited for dressing up with a more solid construction that other similar boots.
Pick #2: Todd Snyder Sanders Chukka Boot
Produced by Sanders, an iconic shoemaker from Northamptonshire, England since 1873, these Chukka boots have a rich heritage that you can tell from first glance. It blends the look and feel of a traditional chukka with the durability and comfort of a sneaker. A chunky crepe sole leads up to a brown suede upper and two-eyelet design fasted with waxed leather laces. And don’t forget the full leather lining.
Pick #3: Alden Chukka Boot
These boots are a bit pricey for some guys, but you can’t go wrong with Alden’s unlined Chukka boot and its prototypical look. The unlined suede uppers provide optimum comfort and breathability, while the Goodyear storm welt construction, stacked leather heel, leather outsole and cork footbed demonstrate a durability that you’ll enjoy.
Best Hiking Boots
Hiking boots became popular, even for non-hikers, when men began to appreciate their sturdy construction (with durable soles, substantial heel support, and full lace-to-toe closures) that combined the ability to withstand hard work while maintaining a cool look. Whether you prefer something more old-school or modern versions on this traditional boot, we’ve got a few selections that most men will prefer.
Pick #1: Danner Light Revival
Featuring a lightweight 1000 denier nylon combined with full-grain leather uppers, the classic Light Revival from Danner feels lighter than most other hiking boots, but it doesn’t go light on performance. The Vibran Kletterlift sole is well-intended for all sorts of tough surfaces, while a unique Gore-text lining helps protect against water.
We like the intimidation factor that comes from the chunky ripple sole, along with the stitchdown construction that will definitely endure. Plus, the full-leather lining and other bold designs make this Italian Alps-style boot a fan favorite.
Here’s an updated version of the traditional hiking boot, thanks to the leather accents that also provide cool wrap-around laces for additional support. The breathable shearling will keep your feet warm and dry during the most frigid winter weather.
Best Hunting Boots
If you’re actually going hunting, you probably would select something a bit more utilitarian for your experience, but if you like the look of hunting boots and enjoy the traditional bits such as a lace-up closure, durable grippy outsole or hand-sewn mock-toes, check out these 3 hunting boot styles that are popular, especially in the Northeast.
Pick #1: Rancourt & Company Sherman Boot
This Sherman Boot from Rancourt stands out amongst the smoother leather accented options out there today. The shrunken bison leather upper suggests a grainy style, which is highlighted by natural lactate hevea crepe soles, and a true moccasin construction that gets better with brass eyelets.
Pick #2: L.L. Bean Original Duck Boot
Since 1912, this “duck boot” has been amongst L.L. Bean’s most popular choices, thanks to quarters made with full-grain leather uppers that provide optimum water protection plus comfort, and a durable rubber outsole.
Pick #3: Russell Moccasin 5.5 “PH”
This is another unique offering that stands out, thanks to Russell’s choice to combine sleek bison leather and tougher cotton duck, which makes for a lighter boot that gives plenty of comfort plus durability. You also can choose from a variety of soles, too.
Best Work Boots
About 50 years ago, shoemakers pretty much perfected the look of the work boot that endures up to today: boots that are strong, last a long time and offer just enough style so that you can wear them with just about anything, especially when the weather’s rough. Most work boots provide a durable lug sole with no-frills lace-up styles that make these a stable of any collection.
Pick #1: Red Wing Iron Ranger Cap Toe Boot
Red Wing made a name for itself by creating durable work boots like this iconic Ranger Boot. With a cork midsole for comfort, speed hooks and Goodyear-welt construction, you also get that much-needed protective cap toe, too. The brand uses its own tannery to finish the look and even though it will require a break-in process, we think it’s worth the wait.
Pick #2: Taylor Stitch Moto Boot
Even though Taylor Stitch tends to market its boots to bike riders, this particular style makes for a solid all-around work boot. The triple-needed stitching is unique, and the combination of Goodyear storm welt construction (assembled in Leon, Mexico) will definitely last. We like the soft, weatherproof snuff suede uppers and an insole, midsole, and welt that features plenty of vegetable-tanned leather and an enduring Vibram lugged sole.
Pick #3: Nick’s Handmade Robert Brown 55
For years, only folks in the Northwest knew about this famed bootmaker, but Nick’s has expanded and can now be found all over the country. That’s probably due to the balance of durability and good looks, since its Robert Brown boot, in particular, gives you a nice leather midsole, sculpted stacked leather heel, brass eyelets and leather lace accents plus the Vibram outsole.
Best Trench Boots
Ever since they were first worn during WWI, the trench boot … also referred to as an officer or army boot … has been cleaned up and become a staple part of any guy’s wardrobe. In similar ways to the work boot, the low-profile silhouette of the trench boot is easy to add to any kind of style… from casual to fancy.
Pick #1: Oak Street Trench Boot
This is Oak Street’s signature boot, inspired by WWII styles made popular in the 1940s and 50s. Made in America with Chromexcel leather uppers that come directly from Chicago’s Horween Leather Company, plus rawhide laces, a leather sole and brass eyelets, this is a handsome trench boot that will appeal to a lot of guys.
One of the best values for a trench boot that you can find, this Diesel boot from Grant Stone will last a long time. With a steel shank and Goodyear-welted construction, you get durability along with comfort from the cork filling and a stylish full-grain leather upper.
The John Lofgren make is well-known and highly regarded in the world of boots, and this M-43 Service Boot is about as good as you can get, unless you’re acquiring actual vintage boots from WWII. Thanks to the historically accurate Munson last that included a natural Chromexcel roughout upper and unstructured toe, this Japanese made boot gives you all the durability you want thanks to a Vibram 705 sole, Vibram 700 heel and Goodyear welt.
Best Cowboy Boots
As you probably know, cowboy boots were first constructed for practicality. The old guys in the West would pull them on, wear them out in the field and count on them to last for years. Traditional cowboy boots give you a taller and angled riding heel, while Roper boots will feature a shorter heel that’s designed more for walking. Of course, nothing can replace the iconic and instantly recognizable pointed toe and tall shaft.
Pick #1: Tecovas Men’s Suede Cowboy Boots
This Johnny boot from Tecovas is offered direct-to-consumer, which helps make quality much more affordable. The water-resistant suede is a nice take on the traditional cowboy boot, and you also get a leather-stacked heel and ¾ Goodyear welt construction.
For more than 160 years, Rios of Mercedes has been crafting cowboy boots that are customer favorites. This Sand Elk Bottom version meets all those legendary criteria, thanks to elegant French binding, a leather-rubber combo sole, Cuban heel and cool Western stitching on the shaft.
You’ll find a bunch of cowboy boots at Heritage Boot Co., and there are basic styles to ones that provide more exotic looks with leather and hand-crafted designs. This Ranch Hand book gives a nicely decorated western stitched upper plus luscious brown suede. The Cuban heel plus dramatically chiseled toes makes it very popular amongst boot lovers.
Best Engineer Boots
Originally, engineer boots were built to protect workers on steam engines from the hazards of feeding coal and other dangerous parts of their job. Like cowboy boots, they tend to come in tall pull-on styles that contain supporting arches and the durable soles you’d find in work boots. The buckled ankle strap is the iconic feature that makes it stand out from other pull-on boots.
Once again, Red Wing comes through with this signature Engineer boot. You’ll get premium Goodyear welt construction at an affordable price plus cork-filled insoles for optimum comfort and durability.
Pick #2: White’s Nomad Boot
Not for the faint of heart, this durable and bulky Nomad Boot stands out from the crowd, and it will definitely turn heads and last a long time, thanks to hardy stitchdown construction, full-leather midsoles and shank, a mini Vibram sole and water-resistant leather upper that adds to its appeal.
Pick #3: Self Edge Flat Heat Boots
You’d never know that these are made in Japan, because it looks so iconically American, but The Flat Head boot may be some of the hardest engineer boots to find. They are only constructed in small batches, but we absolutely love the storm welt construction, steel shanks, custom-made brass hardware and wonderfully crafted Chromexcel pull-up leather.