30 Best Men’s Boots For Every Occasion

Jan 15, 2018

Category: Style

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Not all boots are created equal. Some are better fit for more formal settings while others are tailor-made to get seriously dirty on the job-site or out on the trail.

To help you navigate through the broad variety of types, we built out a list consisting of 8 different styles of men’s boot and included some of our favorite examples from each. Whether you’re looking to grab up a pair of boots for wearing in to work everyday, or you’re interested in what other type of hunting boots may be at your disposal, we’re sure our rundown of the best men’s boots for every occasion will prove a helpful guide.


A Dress Shoe Stalwart

Wingtip boots, or brogues as they’re often referred to, are defined as being any shoe with multiple layers of decorative leather along their upper. That extra layer is perforated and serrated along the edge – resulting in an eye-catching but not altogether loud or in-your-face look, making it ideal for wearing to more formal settings. But this wasn’t always the case. When they were first made, brogue’s were intended to be used as a walking shoe – something to stroll around the country in – making them inappropriate for more formal contexts. So really however you wear these you’ll be fine.

Allen Edmonds Dalton Wingtip Dress Boots

Made from a premium calfskin leather and featuring butyl double leather soles, these American made wingtip boots are ideal for lacing up for either daily or more formal wear. They come in one of five available colors and are built too last a lifetime.

Purchase: $445

Officine Creative Aspen Burnished Wingtip Brogue

These boots feature a decidedly more rugged look to them with deep lugged soles bottoming out the otherwise refined burnished tan leather upper. All things sand these Italian boots are ideal for wearing around the city or daily into the office.

Purchase: $700

Thom Browne Crepe Sole Wingtip Boot

More than just standing out thanks to the attractive perforations in the leather upper, these boots from Thom Browne boast a textured pebble-grain leather upper and comfortable black crepe sole. Those features paired with the colorful pull tab on the back heel make them a truly stand-out pair for those looking to make a statement.

Purchase: $1,125

Chukka Boot

From The Field Of Battle

Chukka boots, like most items in men’s fashion, can have their origins traced back to the battlefield. Initially, these shoes were worn by members of the British military in the battlefields of Northern Africa during the second World War. Since then, they’ve become a popular silhouette both back in the UK and here in the U.S. They’re now made in a variety of different styles, with and without heels, and with everything from canvas to leather uppers.

Clark’s Desert Boot

Among the most recognizable and popular versions of the chukka boot is this pair from Clark’s. They’re crafted from a suede upper, attached to a soft and comfortable crepe outsole, and boast the same overall look and style they were given over 60 years ago.

Purchase: $120

Paul Evans Newman Chukka Boot

This pair of chukka boots from Paul Evans are decidedly more refined than others in this section. They’re made from full-grain Italian calfskin leather and painted one of five colors by hand in Italy. A great pick for wearing casually or in more formal settings.

Purchase: $400

John Lobb Grove Suede Chukka Boots

For a more traditional look in a high-end package, consider this pair from British brand John Lobb. Made by hand in their Northampton workshop, these chukka boots boast a suede upper and grippy lugged rubber outsole.

Purchase: $1,435

Ankle Boot

Top Notch, Low Rise

Unlike most other boots on this list, this style doesn’t really have some long, storied history to it. They’re simply a popular version of a men’s boot that sit either just below or just above the ankle – usually concealing or lacking laces along the mid foot region. Sometimes, even in men’s fashion, things are just straightforward.

Paul Evans Heston Double Monk Strap Boot

These handmade Italian calfskin leather monk strap boots are among the most striking we’ve come across. The gorgeous painted leather contrasts sharply with the metallic buckles – giving them both a striking, and clean look.

Purchase: $400

Common Projects Suede Boots

A kind of version of the chelsea boots from the same brand, this pair features a suede upper with gold serial numbers printed along the heel and a crepe soles for a comfortable fit. A zipper along the inner portion of the shoe is built for easy access.

Purchase: $460

AMI Suede Jodhpur Boots

Not quite a monk strap and not quite a chelsea boot, this pair from AMI feature a clean upper with a strap and buckle along the ankle. That upper is made from a top-tier black suede and fastened to a rubber crepe sole.

Purchase: $595

Santoni Ankle Boots

Ok so we’re stretching a little by putting this one in the ankle-boot category. They’re low enough to qualify as an ankle boot, yet they feature the classic laceless style of a chelsea boot. However you categorize them, these Italian made burnished grain leather boots are great for wearing any time.

Purchase: $660

Chelsea Boot

From Across The Pond

Technically, you can trace these boots all the way back to 1850. They were worn by Queen Victoria and caught on among both men and women until they fell out of fashion at the outset of the first World War. They re-emerged in the 1960s as being the choice shoes of mod scene, and then again more recently in the mid-to-early aughts. Given that they’re so comfortable to wear, it’s no wonder why they’ve stuck around.

Cole Haan Dumont Grand Waterproof Chelsea Boot

This boot from Cole Haan is just about as technically advanced as you can get when it comes to men’s boots. Made from a waterproof leather and paired with a cored out rubber sole that’s filled in with a proprietary cushioning foam, they manage to be both incredibly comfortable and good looking.

Purchase: $300

Paul Evans Dean Chelsea Boot

This pair from Paul Evans is capable of wearing with a more formal getup, or just a pair of jeans. Made from painted Italian full grain leather and attached to a high quality elastic fabric, they’re the perfect pick for daily wear.

Purchase: $400

R.M. Williams Comfort Craftsman Suede Chelsea Boots

Australian label R.M. Williams’ whole things was to create footwear that’s fit for use both in the outback and in the city. These boots reflect that sensibility with their Goodyear-welted soles and resilient suede upper.

Purchase: $495

Common Projects Suede Chelsea Boots

Common Projects has emerged as a great shoe brand in large part due to their ability to do simple styles incredibly well. They haven’t deviated form that trend at all with their chelsea boots. Made from a high quality suede upper an fitted to a crepe outsole, they’re about as good as you can get.

Purchase: $525

Work Boot

Punch The Clock

What is there to say about work boots, really. Built to preform more than anything else, they’ve always put function ahead of form. The only reason we see them in a more style-forward context now is because men’s fashion, and our culture, has a tendency to lionize blue-collar work and up-sell its to whoever’s willing to shell out the duckets.

Thorogood American Heritage Steel-Toe Work Boot

These American made boots from Thorogood feature a MAXwear Wedge outsole that’s oil and slip resistant, as well as a steel-toe for protection from heavy objects. A quality, practical pick for wearing to the worksite or around town.

Purchase: $145

Red Wing Heritage Moc

Red Wing is just about as classic as they come – but maybe too classic for those who work on construction sites. The boot features Goodyear welt construction, a leather upper, and a comfortable outsole. It does not, however, have a steel toe.

Purchase: $214

Chippewa Apache Steel Toe Lace Up

Another pair of American made boots featuring a tough leather uppers, Vibram lugged outsole, and a steel toe cap. They’re purpose-built for hard work and built to outlast just about all others in the same market.

Purchase: $219

Visvim Blackstone Leather Boots

Made from a high quality leather upper and fitted to a shock-absorbing Vibram outsole, these boots manage to be both stylish and capable. A great grab for those who are fans of classic American style and high-end fashion brands.

Purchase: $1,890

Cowboy Boot

For More Than Just Riding

The look and feel of cowboy boots are derived from classic riding boots built for cavalry riders and equestrians. Contemporary cowboy boots can be broken into two sections, classic or ‘roper’. Roper boots feature a shorter, squared off heel measuring less than an inch high and a more rounded off heal. Classic boots, on the other hand, boast larger, tapered heels and much more pointed toes.

Frye Billy Harness Boots

These boots from Frye feature a harness strap along the ankle, a slightly tapered heel, and point toes. The upper portion of the boot is crafted from a stone tumbled and hand polished leather that features a worn in, but fresh look.

Purchase: $358

Heritage Boot Co. Apache Boot

A classic cowboy boot with a snip toe and aggressively tapered heel. The upper is made from a black oil tanned leather with an added matte finish that makes the stitched pattern stand out all the more.

Purchase: $420

Luchesse Statesman Boots

Made by a heritage Texas-based boot maker, these square-healed roper boots feature a brown burnished leather upper with off-white embroidery, leather linings, and a leather outsole. And to top it off, they were the same style of those worn by Matthew Vaughn’s Statesman agents in the most the film Kingsman The Golden Circle.

Purchase: $650

Hiking Boots

Built For Trekking

When it comes to backpacking or hiking, the most essential piece of gear you can have are your boots. They help protect you from cold, harsh weather while providing support and traction for all those miles of walking. While a lot of boots out there are better left on the trail, there are a good deal out there that look just as good 10-miles in to a week-long backpacking trip as they do on your morning commute. Take a look at our grabs right here.

Sorel Ankeny Boots

Built from a waterproof leather upper and featuring tough metallic d-rings for lacing, these boots from Sorel are capable of striking out through all kinds of weather. The vulcanized rubber outsole provides plenty of secure grip whether you’re mucking through wet trails or walking across frozen concrete.

Purchase: $140

Zamberlan Vioz GTX Backpacking Boot

Featuring a tough leather upper lined with Gore-Tex and a Zamberlan Vibram 3D outsole for traction, this boot is built for long, hard hikes. But just because it’s rugged doesn’t mean its stiff. The special flex system makes it so the boot can move to match the motion of your foot and lower leg.

Purchase: $295

Arc’Teryx Bora GTX Waterproof Nubuck Hiking Boot

One of the most innovative outdoor apparel brands out there didn’t just stop at rain jackets and base layers. Arc’Teryx’s Bora GTX boot boasts an external waterproof nubuck leather shell and interior removable booty that can be switched out according to whatever type of conditions you’re hiking in.

Purchase: $300

Danner Ridge Boot

Portland, Oregon-based company Danner produces what we think of as the platonic ideal of the hiking boot. Their look is a classic one – uppers made primarily from leather, and simple but capable outsoles. Danner’s Ridge does not deviate from these theme at all. The handsome silhouette features a Gore-Tex lining, an Ortholite footbed for comfort, and durable stitch down construction. Oh yeah, and it’s all made in the USA.

Purchase: $360

Hunting Boot

Catch Game

Unlike hiking boots, hunting boots need to do more than just get you from point A to B. These boots have to keep you high, dry, and warm while laying in wait for a buck, or wading through shallow water stalking quail. While a lot of modern hunting boots rely on rubber and synthetic textiles to provide the protection and warmth that hunters need, there are still some capable classics out there worthy of wearing out early in the morning.

Cabela Iron Ridge

Featuring a richly oiled waterproof full-grain leather upper lined with GORE-TEX and filled with 800-grams of Thinsulate, this boot is more than capable of keeping you warm and dry even in the roughest conditions. For added versatility, the outsole features an aggressively lugged bob pattern that grips even when wet and icy.

Purchase: $110

L.L. Bean Maine Hunting Shoes

Originally developed as hunting boots for Mainers, this classic silhouette features a rubber outsole and mid foot built to keep your feet dry, and a handsome brown leather lace-up upper that’ll mold to your leg for a custom fit. And to top it off, it’s 100% made in the United States.

Purchase: $140

Columbia Bugaboot XTM Omni-Heat

Looking for something a little more modern? Columbia’s Bugaboot is worth a look. This boot features a bevy of proprietary tech from the outdoor brand including Omni-Heat reflective lining, a Techlite shell and midsole for cushioning and comfort, as well as an Omni-Grip outsole for serious traction. All of those features combined with 600-grams of insulation and a waterproof seam-sealed treatment make these boots a great all around pick.

Purchase: $160

Sorel Caribou Faux Shearling Trimmed Boot

Purpose built to take on even the coldest weather, these boots from Sorel feature a waterproof full grain leather upper and a rubberized mid foot. The interior of the shoe is lined with wool with Sherpa Pile cuffs for keeping warm air in and cool air out. All of this combined with the super grippy AeroTrac outsoles make this a solid cold-weather pick.

Purchase: $170

Yuketen Maine Guide Suede Boots

Inspired by some of the earliest boots worn by wilderness guides in the North East of the U.S., these shoes feature a super soft, comfortable outsole and attractive moccasin-like upper. They’re not quite what you’d expect to see on the feet of a contemporary hunter, but they sure do look good.

Purchase: $615

27 Best Dress Shoes For Men

So you’ve got the rundown on the best men’s dress boots for every occasion. But how about regular dress shoes? Check out our writeup on the best of the best dress shoes.

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