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Types of Men’s Boots: How to Wear Them & Noteworthy Brands

Men have no lack of choice when it comes to types of boots. From the timeless Chelsea boot to the rugged hiking boot, there’s a style of boot to suit every taste. 

So today, we wanted to give you a rundown of the different types of men’s boots available, along with a few style tips on how to wear them.


Here’s a brief side-by-side comparison of all the shoes we’ll be discussing today:

types of mens boots

Additionally, we also put together a table with a more in-depth look at each style of boot, which includes the following details:

  • Boot Type: What category does the boot type fall into.
  • Intent: When and what occasions are they meant to be worn.
  • Key Features: What makes this boot style unique.
  • Common Uppers: Popular materials used on the boot’s upper.
  • Noteworthy Brands: Best-in-class brands that make each style of boot.
Boot TypeIntentKey FeaturesCommon UppersNoteworthy Brands
Ankle BootsCasual to Semi-FormalSide Zip Closure, Sleek Design, Pointed ToeLeather, SuedeBeckett Simonon, Dr. Scholl’s, Skechers
Chelsea BootsCasual to Semi-FormalElastic Side Closure, Sleek DesignLeather, SuedeThursday Boot Company, Beckett Simonon, Steve Madden, Red Wing Shoes
Chukka BootsCasual to Smart CasualLace-Up, Ankle Height, Crepe SoleLeather, SuedeRed Wing Shoes, Thursday Boot Company, Beckett Simonon, Clarks, Cole Haan, Timberland, Nunn Bush
Combat BootsCasualLace-Up, Low to Mid-Calf Height, Rugged SoleLeather, Nylon, SuedeDr. Martens, AllSaints, Prada, Vince, Steve Madden
Cowboy BootsCasualMid-Calf Height, Pointed Toe, High Heel, Leather StitchingLeatherAriat, Justin Boots, Cody James
Engineer BootsWorkwear, CasualLaceless Design, Mid-Calf Height, Steel ToeLeatherWesco, Role Club, John Lofgren
Hiking BootsWildernessRugged Outsole, Ankle Support, Lace-UpLeather, Canvas, NylonMerrell, HOKA, REI, KEEN, Eddie Bauer, Columbia Sportswear, Timberland, Danner, Salomon
Hunting BootsWildernessRugged Outsole, Ankle Support, Lace-Up, InsulationLeather, Canvas, NylonScarpa, LaCrosse, Zamberlan, Schnee’s, Crispi, White’s Boots
Jodphur BootsCasual to Semi-FormalSingle Ankle Buckle, French Toe, Sleek DesignLeather, SuedeBeckett Simonon, The Frye Company, Horze
Motorcycle BootsCasual, SportsTough Materials, Padded Collar, Protection-Centric DesignLeather, Plastic, NylonHarley-Davidson, Alpinestars, Balenciaga, Dr. Martens, Thursday Boot Company, SIDI, TCX, Forma
Rain BootsCasualWaterproof Materials, Non-Slip Sole, No LacesNylon, RubberHunter Boot, Burberry, Sperry Top-Sider, London Fog, Crocs, UGG, Bogs
Riding BootsEquestrianKnee-High Length, Shallow HeelLeatherTecovas, Parlanti, TuffRider, Horze
Safety BootsWorkwearLace-Up, Steel Toe, Slip ResistantLeather, NylonTimberland, Red Wing Shoes, KEEN, Thorogood
Snow BootsCasualLace-Up, Insulated Lining, Varying Heights, WaterproofingLeather, NylonBlundstone, The North Face, Dr. Martens, Kamik, UGG, Sorel, Timberland, Columbia, Moon Boot, Vans
Trench BootsCasual to Smart CasualLace-Up, Ankle HeightLeatherOak Street Bootmakers
Wingtip BootsSemi-FormalLace-Up, Ankle Height, Brogue, Pointed ToeLeatherNunn Bush, Thomas & Vine, Allen Edmonds, Johnston & Murphy
Work BootsWorkwearLace-Up, Ankle Height, Steel Toe, Slip ResistantLeather, NylonBrunt, Ariat, Thorogood, KEEN, Timberland, Caterpillar

Ankle Boots

ankle boots

Ankle boots feature a low heel and an ankle-height shaft like the Chelsea boot. They can be made from various materials, including leather, suede, and canvas. 

However, what differs from Chelsea boots is that they will often have a side zipper instead of an elastic side panel.

How to Wear Ankle Boots

Ankle boots are semi-formal and can be worn with jeans, chinos, and suit trousers (for semi-formal occasions). If you’re going for a more casual look, pair your ankle boots with some raw denim jeans. Then, pair them with some chinos, an oxford shirt, and a blazer for a smart-casual look.


Only a few companies make Ankle boots. The most well-known are probably Beckett Simonon, Dr. Scholl’s, and Sketchers.

Chelsea Boots

chelsea boots

From the Beatles to David Beckham, it’s fair to say that the Chelsea boot is a style icon. They were first made popular in the Victorian era and have been in and out of fashion. Chelsea boots are ankle-high boots that feature an elastic side panel and a low heel. They can be made from various materials, including leather, suede, and canvas. 

Some companies such as Hunter now make rain boots which are Chelsea boots made from rubber – perfect for festivals or days out in the rain.

How to Wear Chelsea Boots

Chelsea boots are semi-formal and best worn with raw denim or chinos. For a more formal look, pair your Chelsea boots with a suit.


A few brands that make Chelsea boots include Thursday Boot Company, Beckett Simonon, Steve Madden, and Red Wing Shoes.

Chukka Boots (Desert Boots)

chukka boots

The Chukka is a traditional boot worn by British Soldiers during the Western Desert Campaign during World War II (source). Chukka boots are ankle-high with two or three eyelets, leather or suede uppers, and crepe soles. 

They’re the perfect mix of smart and casual and can be worn with jeans, chinos, and suit trousers. 

How to Wear Chukka Boots

Chukka boots are semi-formal and look great with raw denim jeans or chinos. Should you want to dress up a bit, then wear Chukka boots with a blazer. But they should never be worn with a suit, to an interview, etc.


Several brands make great chukka boots, including Red Wing Shoes, Thursday Boot Company, Beckett Simonon, Clarks, Cole Haan, Timberland, and Nunn Bush.

Combat Boots

combat boots

If you prefer a more tactical look, combat boots are for you. They were originally designed for military personnel but have become a fashion staple. Designed by some of the most luxurious fashion brands globally, including Prada, Vince, and AllSaints, these boots feature a chunky sole, lace-up closure, and often multiple straps. 

They’re made from tough materials such as leather and nylon and feature a lace-up front, metal eyelets, and a rubber sole. 

How to Wear Combat Boots

While designed by luxury brands, these boots are purely casual and shouldn’t be worn with anything other than jeans or cargo pants. Purely streetwear.


If you’re looking for high-end combat boots, check out Dr. Martens, AllSaints, Prada, Vince, and Steve Madden.

Cowboy Boots

cowboy boots

Yeehaw! Nothing says America quite like a good old pair of cowboy boots. First made popular in the American West, these boots feature a pointed toe, high heel, and often decorative stitching. Rising to approximately mid-calf, they’re made from tough materials such as leather and are designed to withstand wear and tear. Despite their western roots, they’re now worn all over the world.

How to Wear Cowboy Boots

While cowboy boots still have a strong association with the American West, they can be worn with various looks. Pair them with some raw denim jeans and a plaid shirt for a casual look. And for a true western look, pair them with a leather jacket, a proper cowboy hat, and some bell-bottom jeans.


A few brands make cowboy boots, including Ariat, Justin Boots, and Cody James.

Engineer Boots

engineer boots

For the hardworking men who take care of our infrastructure, we have engineer boots. These boots were designed for – you guessed it – engineers but have become popular in the fashion world. They often feature a cap toe, are made from tough materials such as leather, and have a lug sole. Absent of any laces, they slip on and off easily, perfect for those who are always on the go.

How to Wear Engineer Boots

Engineer boots are primarily made for workwear but can also be worn in a casual setting. Pair them with some raw denim jeans, a denim jacket, and a t-shirt. 


Very few brands make engineer boots, but a few include Wesco, Role Club, and John Lofgren.

Hiking Boots

hiking boots

Whether for weekend outings or long treks through the mountains, hiking boots are necessary. Unlike other types of boots, they’re designed for function over form and feature a thick sole, waterproof materials, and a lace-up closure. No fashion statement is necessary with these boots. Upper materials can include leather, canvas, and nylon. Lastly, they rise above the ankle to prevent injury and protection from low-hanging branches, etc.

How to Wear Hiking Boots

Hiking boots are designed for the great outdoors and will often be paired with a backpack, some shorts, and a t-shirt. Just pair them with the right type of socks to prevent blisters. 


A few notable brands that make hiking boots, include Merrell, HOKA, REI, KEEN, Eddie Bauer, Columbia Sportswear, Timberland, Danner, and Salomon.

Hunting Boots

hunting boots

Very similar to hiking boots, hunting boots are designed for – you guessed it – hunting. They often feature a camo print and rise above the ankle for added protection. They’re made from tough materials such as leather and canvas and have a thick sole like hiking boots. They also may provide additional insulation to keep feet warm while waiting in the woods for prey.

How to Wear Hunting Boots

Given that these are designed for hunting, they pair well with a camo print jacket, some jeans, and a t-shirt. 


Several brands make hunting boots, including Scarpa, LaCrosse, Zamberlan, Schnee’s, Crispi, and White’s Boots.

Jodphur Boots

jodphur boots

Named after the city of Jodhpur in India, these boots are also known as paddock boots or equestrian boots (source). They feature a low heel, slip on and off easily, and have a classy French toe box. The single buckle that goes across the ankle gives these boots their signature look. Like Chelsea boots, you’ll find that Jodhpur boots are made primarily from leather or suede.

How to Wear Jodhpur Boots

The sleek and streamlined appearance of Jodhpur boots makes them a great choice for various looks. For a more casual look, pair them with some raw denim jeans, a leather jacket, and a t-shirt. And for a dressier look, pair them with tailored trousers, a blazer, and a dress shirt.


There are a few brands that make Jodhpur boots, including Beckett Simonon, The Frye Company, and Horze.

Motorcycle Boots

motorcycle boots

Whether you ride a Harley-Davidson or a Ducati, motorcycle boots are a must. However, motorcycle boots vary greatly in style. From a beautiful leather lace-up design to a much more functional racer style (ex: SIDI), there is a boot for every rider. 

But what they all have in common is that they’re made from tough materials, have a thick sole, a padded collar, and often rise above the ankle for added protection. 

How to Wear Motorcycle Boots

Motorcycle boots can be worn both on and off the bike. Just about all of them go well with denim or black chinos, a t-shirt, and a leather jacket. 


Plenty of brands make motorcycle boots, including Harley-Davidson, Alpinestars, Balenciaga, Dr. Martens, Thursday Boot Company, SIDI, TCX, and Forma.

Rain Boots

rain boots

It’s raining, it’s pouring…and you don’t want your feet to get wet. That’s where rain boots (Wellington boots, duck boots, or gum boots) come in. These rubber (or plastic) boots will keep your feet dry while walking through puddles or trudging through the snow. And they come in a variety of colors and designs to suit your style. They also vary in height and can be either ankle-length or knee-high.

How to Wear Rain Boots

Rain boots are best worn in tandem with a proper raincoat. If you want to look dapper, we recommend a pair of Hunter rain boots. Or, for more fun and funky look, go for a pair of Joules rain boots.


Several brands make rain boots, including Hunter Boot, Burberry, Sperry Top-Sider, London Fog, Crocs, UGG, and Bogs.

Riding Boots

riding boots

Not to be confused with motorcycle boots or cowboy boots, riding boots are intended for riding horses. This equestrian footwear is both functional and stylish. The knee-high cuff protects the rider’s leg from getting scraped by the stirrup while riding. And the heel helps keep the foot from slipping through the stirrup.

These aren’t commonly worn outside of the horseback riding arena. But, if you’re looking for a unique and stylish boot, riding boots may just be the way to go.

How to Wear Riding Boots

Given that riding boots are intended for, well, riding horses, they’re not commonly worn as everyday footwear. However, if you want to give them a try, we recommend pairing them with skinny jeans and a leather jacket.


Some brands that make riding boots include Ariat, Tredstep Ireland, Mountain Horse, Dublin, and Equine.

Safety Boots

safety boots

While some may refer to safety boots as their type of boot, they are really just a subset of work boots. But what sets them apart is that they have additional safety features to protect the wearer from on-the-job hazards. This can include a steel toe, a slip-resistant sole, or electrical hazard protection.

How to Wear Safety Boots

Safety boots are intended for work, so they’re best worn with utility jeans, a hard-wearing shirt, and a jacket. 


Plenty of brands make safety boots, including Timberland, Red Wing Shoes, KEEN, and Thorogood.

Snow Boots

snow boots

With a name like snow boots, it’s pretty obvious what these are for. But in case you’re new to the game, snow boots are made to keep your feet warm and dry in cold and snowy conditions. They typically have a water-resistant upper, a thick sole, and insulation. Insulation can either be built into the upper or feature a cushy shearling lining. Available in varying heights from ankle to mid-calf, they’re also great for trudging through deep snow.

How to Wear Snow Boots

Snow boots are best worn with thick socks. But, of course, if you are looking to make a fashion statement, you can always go for snow boots from brands such as Moon Boot or UGG.


Some snow boots brands include Blundstone, The North Face, Dr. Martens, Kamik, UGG, Sorel, Timberland, Columbia, Moon Boot, and Vans.

Trench Boots

trench boots

Also known as Pershing boots, American soldiers wore trench boots in World War I. These heavy-duty lace-up boots were designed to protect the soldier’s feet from the elements while in the trenches. 

Trench boots are made of thick leather with a water-resistant finish. And they often feature a steel toe and a lug sole for traction.

How to Wear Trench Boots

Trench boots are best worn with utility jeans or trousers. These boots demonstrate a no-nonsense style, so it’s best to keep the rest of your outfit fairly simple.


Very few brands still make trench boots. But, if you’re interested in giving them a try, we recommend checking out Oak Street Bootmakers.

Wingtip Boots

wingtip boots

Wingtip boots are a stylish and sophisticated option with a distinctively pointed toe and an intricate brogue design. These boots are considered dress boots and are best worn with semi-formal attire. However, we still would recommend traditional Oxford or Derby dress shoes for more formal occasions.

Rising above the ankle, Wingtip Boots feature a lace-up closure and can be made of either leather or suede.

How to Wear Wingtip Boots

Wingtip boots are best worn with trousers, a dress shirt, and a blazer. You can pair them with dark denim and a sweater for a more casual look. Just be sure to wear them with the right type of dress sock.


A few men’s formal footwear brands that make wingtip boots include Nunn Bush, Thomas & Vine, Allen Edmonds, and Johnston & Murphy. 

Work Boots

work boots

As the name implies, work boots are designed for working men. These heavy-duty boots are made to protect the feet from on-the-job hazards and usually feature a steel toe, a slip-resistant sole, and electrical hazard protection. Work boots run the gamut for material and may be made of leather, suede, or nylon. These are purely functional boots, but some brands have put a fashionable spin on them.

How to Wear Work Boots

Pair work boots with utility jeans and a hard-wearing shirt. If you want to look stylish in your work boots, choose a pair with a more modern silhouette and clean lines.


Check out Brunt, Ariat, Thorogood, KEEN, Timberland, and Caterpillar if you are looking for a pair of stylish and well-made work boots.

Common Questions

What are the most versatile boots for men?

The Chelsea boot is the most versatile boot for men. It can be dressed up or down and looks great with a variety of different pants, from jeans to dress trousers.

How many boots should a man own?

It depends on several factors. At a minimum, we recommend having dress boots and casual boots. However, there are instances where more boots should be added to the wardrobe such as for work, bad weather, or specific activities.

How do you break in new boots?

There are a few ways to break in new boots. The most common is to simply wear them around the house for a few hours each day until they feel comfortable. Another way is to use a boot stretcher or shoe trees.

About Adam

As the lead editor of Tools of Men, Adam is an expert in all things men's grooming and style. When you don't find him reading up on the latest style trends, he likes to go jogging, attempt to distinguish the differences between IPAs, and play sports with his kids.

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