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The best men’s boots for anyone who cares about style

Upgrade your boot game with these options

Brown chukka boots on rocks
Jeremy Yap / StockSnap

As the weather changes to the colder time of the year, your feet need a little more protection than your sandals can offer. Naturally, that means you’ve put your sandals, boat shoes, and loafers to the side while you introduce your boots back into your wardrobe. Of course, there are all kinds of boots on the market, and most of them are meant for the more functional side of life. That doesn’t mean you have to sacrifice fashion. Whether you’re looking for functional men’s boots or fashion-forward options, these are the six types of boots and our three options you should focus on for a good marriage of both.

Nisolo Emilio Chukka boots

Best chukka boots

Like many of our favorite menswear items, chukka boots can trace their lineage back to military origins. Of course, you don’t need to be a British soldier in the deserts of Africa or India to enjoy your own chukkas. These are some of the most perfect types of boots for everyday wear, as they can go with virtually any casual outfit. Here are our three favorite selections.

Beckett Siminon Laval chukka boots
Beckett Simionon

Beckett Siminon Laval

Beckett Siminon is one of the companies you should have on your radar if you love stylish options with the goal of saving the planet. It makes everything to order, so there is little waste, and you can rest assured they are made specifically for you. Add to that a pair of chukka boots that can look great with your jeans and leather jacket or your sport coat, and you have a stellar pair of boots to kick off the season.

Man wearing Astorflex Brownflex
Huckberry / Astorflex

Astorflex Brownflex

If you are looking for something to make you feel masculine and still have enough comfort and functionality to keep you moving, Huckberry is one of your go-to brands. These desert chukkas harken back to the origins of these stellar boots and are about as classic as they get. Huckberry worked with Astorflex to combine customer feedback with six generations of expertise to bring you this stellar option for your boot closet.

Clarks Beeswax Desert chukkas

Clarks Beeswax Desert

If you want to make a splash this year in your own sphere of influence, consider picking up shoes that became a global phenomenon and made a splash on the entire world three-quarters of a century ago. The Beeswax Desert hit the scene in 1950 and took a design homaging an Egyptian bazaar to the top of the industry as it was worn by everyone from rockers to beatniks in Europe, Asia, and the Caribbean. Now you can take that phenomenon and bring it to your own world by adding it to your boot rotation.

Chelsea boot in the woods
Hamza Bounaim / Unsplash

Best Chelsea boots

You can thank The Beatles and The Rolling Stones for your favorite slide-on boots as they are almost solely responsible for their resurgence in the swingin’ ’60s. While the British rock-and-roll scene may be the place they started, you can choose to wear them with everything in your closet. Whether you swap out your sneakers with a solid pair of suede Chelseas or you swap out your dress shoes with an elevated leather pair for your suit, they will be your favorite go-to boots.

Portland Leather Almost Perfect Chelsea boots
Portland Leather

Portland Leather Almost Perfect

When you think of a brand like Portland Leather, you think of some of the most perfect shoes you can find on the market. That means it can feel a little jarring when you see a name like Almost Perfect on the product. Rest assured, it would be considered perfect in 99 out of 100 brands, but Portland Leather holds itself above the rest and offers this almost there, but not quite option at a premium discount. One look at these Chelsea boots and your brain will start calling it the Nearly There but Not Quite Only Because of Extremely High Standards but Perfect to Me boots.

Man wearing Blundstone Rustic on fence

Blundstone Rustic

The idea of Chelsea boots is that they can take the place of everything from sneakers to dress shoes. These boots may look casual and be rustic by name, but they will dress down a suit or a sport coat with the best of them. If you start wearing these to the office, you may not even want to make the drive in. The more you wear these boots, the more rustic and casual they will look, so enjoy the life span that lasts about as long as you do.

New Republic Ventura Chelsea boots
New Republic

New Republic Ventura

It’s easy to throw on a pair of sneakers with your denim and T-shirt when you are heading out for the day. But consider that you never know who you will meet, and you only get one chance at a first impression. If you want to make a great first impression, you can ditch the sneakers and go with these suede Chelseas to up your game and make everything look thought out and intentional. If you have a casual first date coming up, this matters.

Dress boots on a counter
Noah Smith / Unsplash

Best dress boots

Dress shoes can span the entire spectrum of shoes from loafers to boots. The main difference between traditional dress shoes and dress boots is the higher shaft that goes above the ankles instead of below. Think of these as the perfect marriage between dress shoes and Chelseas. These three options are sure to make you want to dress up more simply so you can wear them.

Bruno Magli Angiolino Dress Boot
KC Stone / The Manual


Dress shoes can get boring. Sometimes it feels like you can only choose basic colors like black, brown, or cordavan. But with dress boots come new ideas of what style looks like, and these Angiolini boots from Bruno Magli define what style means. Whether you are wearing a suit or want to dress up a casual outfit, these speak for themselves, much like the global reputation of the company that provides them.

Allen Edmonds Hamilton boots
Allen Edmonds

Allen Edmonds Hamilton

Speaking of global reputation, it’s hard to get a better one than what Allen Edmonds enjoys. After a century of knowledge and experience on how to make your feet look and feel like a million bucks, this company knows better than anyone the importance of style and comfort. The Hamilton takes the brogue Oxford design and lifts the shaft past the ankle for a look that will take any outfit to the upper limits of style.

Florsheim Renegade Wingtip boots

Florsheim Renegade Wingtip

Over 100 ago, Florsheim opened doors that would eventually lead to it providing boots to soldiers all through World War II. It eventually changed its focus to appeal to the more stylish man, and the Renegade line is a part of that everlasting tradition. While the line features everything from dress shoes and Chelseas to chukkas and dress boots. these wingtip boots take the tradition of dress shoes and fashion-forward dress boots and combine them into one of the best pair of boots you’ll have.

A man in jeans and brown boots at a park
StepPro / Adobe Stock

Best rugged boots

Look, you can’t always spend your time having dinner with friends or doing touristy things in the city. Sometimes, you have to get out into nature and find a more rugged lifestyle. While you are experiencing the more rugged sides of life, you need a more rugged boot to do so. What do we mean by rugged boots? We mean these three options that will look perfect with your denim at a backyard barbecue or out in the woods on a camping trip.

Thursday Boots Captain
Thursday Boots

Thursday Boots Captain

Boots are your most functional footwear option when you need to get outside. Of course, that doesn’t mean style goes out the door. Instead of looking for any run-of-the-mill rugged boots to fill one need or the other, Thursday Boots has released the Captain to bridge the gap and bring the fashion to the function. These boots won’t work very well with the suits in your closet, but they will transform any other outfit into the pinnacle of masculine capability.

Overland Telluride Bison Leather boots
Overland Sheepskin Co.

Overland Telluride Bison Leather

While Overland Sheepskin Co. may be best known for its leather coats and for becoming the king of ski towns, it is also no stranger to providing customers with everything they need to conquer the mountain. While there are a slew of wonderful options for boots on this list, there is only one made with bison leather, which means this pair of boots will last forever and never look too worn.

Filson Uplander boots

Filson Uplander

Style can feel wasted when you are indoors all the time, which is why Filson has spent the last 100 years producing some of the best outdoor gear and apparel for those who live and work with the sun and stars always in sight. While these rugged boots are durable enough for your outdoor life with a tall shaft to protect and support your ankles, they also feature a moc toe that sets them apart from other boots and will keep you looking stellar even when in the company of others in town.

Man wearing stone chelseas
Brook Cagle / Unsplash

Best fashion boots

Now that we have talked about the rugged outdoors and wilderness exploration, we can go to the other side of the spectrum and look at boots that are meant to be statements. Fashion boots can be any form of boots, but they stand apart by being unique in pattern, color, or design. These three boots will make a statement for you and make you the center of attention no matter what crowd in which you find yourself.

Taft Rome boots

Taft Rome

Taft is one of the best places to go when you are ready to make a statement with your shoes. While it offers everything from floral designs to plaid and paisley, we love this monochrome floral option, as it will make a subtle statement while continuing to be perfect for virtually every outfit you put together.

Embassy London Wanderer boots
Embassy London

Embassy London Wanderer

One of London’s trendiest stores since 2011, Embassy London encourages everyone to step out of line with one of its popular and eye-catching options. The Wanderer is one of the company’s most unique looks, as it features multiple colors and textures in one shoe. The combination of every look you could want on your feet at the same time makes this one of the more complicated boots you can wear, but if you keep the rest of your outfit simple, then this one will speak for itself.

Lethato Zipper boots

Lethato Zipper

We are living in a world that makes it easier and easier to get lost in a crowd. Looking your best and making statements is what Lethato has lived by for the last decade, and it continues that with these fashion boots. Not only is there a zipper in place of the usual laces, but each boot is hand painted in a two-tone style that gives a completely unique look.

Man in black boots
Clay Banks / Unsplash

Best work boots

You work hard. You put in the hours, and you love yourself a good pair of boots while you do. Of course, it’s easy to think that a good work boot isn’t meant for stylish outfits. However, if you find the right ones, they can look just as good with your denim and chinos as they will while you’re building a skyscraper or welding a masterpiece. Here are three of the best boots to find the marriage between work and play.

Man wearing Wolverine 140th Anniversary 1000 Mile bootd with rolled pants

Wolverine 140th Anniversary 1000 Mile

It isn’t hard to imagine the kind of functional boots needed in the Old West. Wolverine was one of the first to recognize the need, and 140 years ago, it created the first work boot, the 1000 Mile. Named for their ability to last for as long as it took to walk that far, these boots stood the test of time and now are back with an anniversary edition. Not only do they work great, but they look even better as these bridge the gap between function and style.

Nicks Boots Trooper Munson Inspired
Nicks Boots

Nicks Boots Trooper Munson Inspired

Nicks Boots has made a living by providing some of the best boots ever made in the country to some of the bravest to wear them. Chosen by firefighters while they keep the Pacific Northwest safe from fires that rage out of control, they are always ready for a mission. These boots are a combination of two of the company’s most popular models and will look fantastic with any jeans or chino you have, whether on a mission or not.

Man rolling jeans up over Ariat boots
KC Stone / The Manual

Ariat Frontier Chimayo

It’s about time that Western boots have their day in the sun. Long since relegated to the fields and barns of the rural areas of the country, these are some of the most comfortable options you can get on the market. Ariat has been one of the primary providers of cowboy boots to the hardest-working men in the country. Named after Triple Crown winner, Secretariat, this company knows what it takes to work hard. For an added flare, Ariat is leaning into the Southwest motif with the Frontier Chimayo.

Boots are versatile, durable, and stylish. Just because the weather is getting colder and the days are getting shorter doesn’t mean you have to sacrifice your style. Some of the best shoe wardrobes will have one of each of these types of boots. These are the 18 best men’s boots for you to wear in 2024 and beyond.

Editors' Recommendations

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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