The 10 Best Types of Boots for Men to Buy

In this post, we’ll discuss the 10 best types of boots for guys and share ideas for a perfect three-boot collection.

If you’re building up your boot collection or buying your first pair of boots, you might be wondering which type of boots to buy.

There are so many different types of boots, from chukkas to Chelseas, and it can be confusing trying to figure out which ones fit into your wardrobe and aesthetic.

Obviously, it depends on your lifestyle. The business professional is going to have slightly different requirements than the college student.

But I think that there are three types of boots that pretty much any type of guy could get a lot of wear out of. If I were starting from scratch, these are the boots I would buy first (in no particular order).

The 10 Best Types of Boots for Men

Here they are…

#1-2: The Work Boot / Service Boot

The dressy work boot or service boot is a great first boot for anyone. I say “dress” work boot because, while this type of boot is styled after a work boot, it’s not necessarily meant to be used for manual labor.

Just like many types of boots (and other fashion-related products, such as jeans), the work and service boots are products of utility – in this case, intensive manual labor and military training/service (and combat).

While these boots could take a beating, these days they’re mostly used to create stylish outfits with rugged, masculine vibes – and they’re perfect for that.

Simply put, these boots are handsome. Personally, I think this dark brown color is a great first choicer most guys, although black is a good option if you wear a lot of black, white and grey.

Dress work boots look awesome with jeans (pretty much any wash), chinos and even trousers if done correctly.

But I’d probably avoid this type of boot in business casual settings, and they should definitely be avoided during formal settings.

The only other time you wouldn’t want to wear these is with shorts, but that goes for pretty much all boots.

Unless, of course, you’re a carefree man-child who has completely given up on his appearance!

#3: The Chukka Boot

The chukka boot is basically just an ankle-high boot. It’s often used to describe desert boots, which are a specific type of chukka.

Desert boots are ankle boots with crepe soles and soft suede uppers. They were worn by British soldiers in North Africa during WWII.

Desert boots, like the J. Crew Macalister, are usually pretty casual, while chukka boots can be pretty dressy.

The big difference is the sole and the upper. For example, this pair of Thursday Boot Co. chukka boots has a structured upper, rather than the soft upper of the Macalisters.

If you got this pair in black leather, it would be pretty dressy, compared to a grey suede desert boot.

I think a standard chukka boot is a great choice for anyone – from college students to business casual professionals. If it’s your first boot, I would go with dark brown.

If you’re expanding your collection, consider suede instead of leather. But make sure you find water-resistant suede if you live somewhere that rains a lot.

Regardless of whether you go with suede or leather, chukkas look great with jeans and chinos. They’re similar to dress work boots but a step up in terms of formality (which makes them more appropriate for office settings).

#4: The Chelsea Boot

The Chelsea boot is cool because it can worn in place of work boots or chukka boots, but it can also be dressed up a bit more, especially if you go with dark brown or black leather.

In fact, it’s not uncommon to see men wearing Chelsea boots with suits these days.

So, if you’re a working professional in a somewhat formal office setting, or if you live in a fashion forward city like Melbourne, London or New York, you might consider buying a pair of Chelsea boots first.

On the formality spectrum, they’re closer to chukka boots than work boots, but you can still dress them down.

Of course, it depends on the material and color. For example, tan suede Chelsea boots with lighter wash jeans is a classic combination.

I really like the light brown suede Chelsea, so if you’re looking to add some variety to your shoe collection, this would be a solid choice.

Either way, the Chelsea boot is a classic, versatile boot that’s easier to pull off than most men think.

And I mean that literally, by the way. Since it has no laces, this boot is very easy to put on and take off, which also makes it great for air travel.

#5: The Moc Toe Boot

Moc toe boots are the ultimate casual boot. They’re really hard to dress up, but you never have to worry if a moc toe boot will go with a t-shirt (it will).

Moc toe is short for – you guessed it – moccasin toe. This toe design is modeled after traditional Native American footwear with a U-shaped design around the toe box.

These boots are typically made with a wedge sole. This spongy white sole is often made from crepe rubber, and it’s flat so that the heel can’t catch on stuff when you’re walking around a job site.

For this reason, some people consider moc toes boots to be work boots, but due to the unique aesthetic, I’m putting them in their own category.

The Red Wing Classic Moc is probably the best example of a modern moc toe boot. They’re crazy popular, especially since the Oro Legacy version has been spotted on taste maker celebrities like Ryan Gosling and Drake.

If you want a premium quality alternative to Red Wing’s Classic Moc, check out the Grant Stone Brass Boot. It’s just a tiny bit sleeker and easier to “dress up” than Red Wing mocs, but the build quality is equally strong (maybe even stronger).

#6: The Dress Boot

A dress boot is basically just a dress shoe with a taller shaft (usually around six inches). Just like with dress shoes, there are many different dress boot styles, including Oxfords to brogues to wingtips.

You can also find dressy Chelsea boots, which are sort of like wholecuts, and dressy chukka boots that have a sleek enough silhouette to wear with a suit and tie.

But the quintessential dress boot is something like the Allen Edmonds Dalton, a lace up wingtip derby with a Dainite rubber sole.

Under a pair of wool trousers, most people wouldn’t be able to tell that these are boots, which makes them perfect for business casual office wear during fall and winter.

The Balmoral boot is another classic dress boot. It’s basically a tall Oxford dress shoe, which makes it more formal than derby style boot or wingtip.

These may have a plain toe, cap toe or some sort of broguing on top of the toe box.

On the higher end, Carmina sells several Balmoral boot styles, all of which are incredible. For a wallet-friendly alternative, check out Beckett Simonon.

#7: The Hiking Boot

Whether or not you enjoy traversing the great outdoors, you might consider adding a hiking boot to your collection.

These are casual, rugged and often lightweight boots that are built for comfort and durability against the elements (i.e., they’re usually waterproof).

If you’re used to wearing heavy leather boots, a hiking boot will make you feel like you’re walking on clouds.

These boots come in a bunch of different styles. If you’re a true hiker, you might want to stick with specialty brands like Merrell, KEEN and Timberland.

If, like me, you don’t need a boot to take on the Arizona Trail, but you do like the hiking boot aesthetic and want something that can take at least some abuse, here are some good options:

The Season Three Ansel is a cool looking lightweight boot modeled after European hiking boots.

Thursday Boot Co. Commander is modeled after old-timey alpine hiking boots, but it has a plush leather collar and Vibram outsole for modern comfort.

Danner’s Mountain Light collection might be the perfect marriage of function and form with its one-piece full grain leather upper, GORE-TEX liner and Vibram outsole.

#8: The Winter Boot

Most guys don’t need a dedicated winter boot. Any Goodyear welted boot or hiking boot will do just fine to keep your feet dry and warm, especially when combined with a good pair of boot socks.

But if you live in a place that gets a true winter every year – like multiple feet of snow – you’re going to want a real winter boot.

Winter boots are lined with some sort of insulating material, such as shearling or Thinsulate (or both).

The upper is typically double- or triple-stitched to the bottom, sealing the boot against water and slush.

Most winter boots look like winter boots. They’ll keep you comfy and safe during a snowy commute to work, but they might not be the best choice for a full day at the office.

There are some winter boots, like the Allen Edmonds Alpine Cap Toe that look like regular boots but are built to withstand the elements.

But most winter boots are noticeably more bulky and rugged than the other types of boots on this list.

If you’re in the market for a pair of winter boots, here are some good options:

• L.L.Bean Boots
• Sorel Caribou Boot
• Pajar Trooper Boot
• The North Face Tsumoru Boot

Any of those will you through even the most punishing winter without totally sacrificing style.

#9: The Jodphur Boot

Jodphur boots kind of look like Chelsea boots, and if you’re wearing pants (which I assume you will be), most people won’t notice the difference.

But Jodphurs do have one unique detail that sets them apart from Chelseas: the ankle strap and buckle.

Unlike Chelseas, Jodphurs lack the elastic wide panel. Instead, they can be tightened or loosened using the ankle strap.

Originally designed in 1920s India for polo players, Jodphur boots are now a lesser known alternative to Chelsea boots and chukkas. Compared to work, service or moc toe boots, Jodphurs are pretty dressy.

They’re great for anyone who like the clean look of Chelsea boots but wants the ability to tighten the shaft around their ankle.

If you want a pair of (somewhat) affordable Jodphurs, check out the Beckett Simonon Douglas Boot.

If you want something a bit more, how do say, baller…check out Carmina’s collection of Jodphurs.

As you can see, they have many different options.

#10: Combat Boots

Combat boots are very similar to service boots in that they were originally designed to be worn by soldiers during military training and service.

Of course, if you’re not in the military, you can still buy combat style boots for casual everyday wear.

These tend to be a bit more rugged and heavy duty than service boots, as they were originally developed to stabilize your ankles, protect your feet, and provide plenty of grip over uneven and/or slippery surfaces.

Combat boots usually have grippy rubber outsoles, water resistant seams and extra room in the toe box for thicker socks.

The Thursday Boot Co. Explorer is a handsome modern take on a classic combat boot.

Of course, any Dr. Martens boots will have that “fashion combat” aesthetic, but your mileage may vary with long term quality and wearability.

Building a Well-Rounded Boot Collection

Since these three boots can often be used interchangeably, I recommend varying up the colors and materials. For example, your collection could consist of:

1. Dark brown leather service boots
2. Midnight suede chukkas
3. Tan suede Chelsea boots

Here’s what that would look like:

But if your style aesthetic is more of a monochromatic, black/white/grey vibe, you could go with something like:

1. Black leather work boots
2. Grey suede chukkas
3. Taupe suede Chelsea boots

This way, you have a variety of styles, colors and materials to choose from.

Once you figure out which boots you tend to wear most often, you can always add another option to the mix. For example, I love having the grey suede desert boot as a more casual alternative to the dark blue chukka.

Your Turn

What kind of boots do you wear? Do you prefer chukkas or Chelseas? Let me know in the comments section!

Questions About Types of Boots

Here are the answers to some questions you may have about boots:

What is the best boot for everyday wear?

The best type of boot for you depends on your style. However, you really can’t go wrong with a chukka or Chelsea boot.

What is the best three boot collection?

If you want a few versatile pairs of boots, you can choose a few different boot styles that are different colors. For example, if you own dark brown leather service boots, midnight suede chukkas and tan suede Chelsea boots, you’ll be set for most occasions.