16 Types of Boots Every Guy Should Know About

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William Barton Avatar by  William Barton | Last Updated:  Sep 17, 2020
Types of Boots Cartoon of a row of boots hanging on boot hangers

Dressing for a fancy occasion? There’s a boot for that.

Getting ready to stand in mud for hours on end. You know there’s a boot for that. 

But knowing which type of boot is right for any given occasion can be tricky. 

That’s why we’re diving into the 16 types of boots every guy needs to know about before they pick up their next pair. 

16 Types of Boots for Men

Chelsea Boots

MGemi dritto chelsea boot model wearing chelsea boot and jeans

What makes them unique?

The most defining characteristic of the Chelsea boot is its elastic sides. Typically, these shoes have one or two pieces of leather wrapped around the entire foot and sewn at the back. 

They became popular in the early ‘60s when The Beatles started sporting them onstage during their concerts.

While they’re no longer known as “the Beatle Boot,” they’ve remained a staple in many fashionable guys’ wardrobes. 

Their sleek silhouette blurs the line between casual and dressy (you’ll find brands that lean more one way than the other), which makes for a versatile boot.

When should you wear them?

Chelsea boots are great because you can wear them with almost any outfit. I prefer them under a pair of tapered jeans, but they work just as well with chinos. 

Many brands craft two distinct styles of Chelsea boots: one bulkier that fits well in a casual outfit, and another slimmer and sleeker that can even be paired with a suit. 

For an example, compare the Thursday Duke and Cavalier. The Cavalier is taller, slimmer, and has a more narrow toe-box. Because of the sleek profile, the Cavalier can sneak its way into a more formal outfit. The Duke, on the other hand, is just too bulky for suits. 

I prefer the slimmer look. It’s more versatile and looks just as good paired up with jeans.

Our Top Picks:

The Chelsea boot evolved slowly, so there’s no single brand that really put them on the map. But here are three brands that are doing the style justice today:

Chukka Boots

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What makes them unique?

Chukka boots are simple, unlined ankle-high leather boots with open lacing and just a few eyelets. They typically have a very round toe-box and thin soles. 

There’s some confusion around the difference between a chukka and desert boot, and it’s easy to miss what separates the two. 

A Desert boot is a Chukka. But it has a rubber crepe sole, and not a vulcanized rubber or leather sole. We’ll get more into the specifics of Desert boots later, but an excellent rule to go by is: all Desert boots are Chukkas, but not all Chukkas are Desert boots. 

When should you wear them?

Chukka boots range in their formality, but they’re really best in casual wardrobes. It’s important to get high quality boots because the toe-box can often stretch, collapse, and look floppy. 

Some brands make Chukkas that can pair with suits, but the style you’re likely familiar with matches a set of chinos or jeans much better. 

These boots are excellent for spring, summer, and fall, but they don’t offer a ton of protection from the elements during winter. 

Our Top Picks:

Clarks made the most popular Chukka, the Desert Boot (read our review), but those are iconic enough to deserve their own section.

Clarks Desert Boot

Clarks Original Desert Boot is the iconic style that put chukkas on the map. It's been 70 years since these went into production and they're beloved around the world.

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Here are some other brands that make excellent Chukkas today:

Desert Boots

Model wearing Clarks Desert Boots and lifting one boot on stairs

What makes them unique?

As I mentioned earlier, Desert boots are a specific style of Chukka boots. While the leather construction is the same, the difference is in the sole. 

Desert boots have a crepe rubber sole instead of a vulcanized rubber or leather sole. 

Crepe soles are much softer than other types of soles so if you’re on your feet for lengthy periods of time, consider this style. However, the soles wear quickly on cement and asphalt. 

When should you wear them?

Just like with Chukka boots, Desert boots are a casual boot. While some brands make Chukkas that don’t look out of place with a suit, you’ll be hard pressed to find a Desert boot that dresses up really well. 

Our Top Picks:

Service Boots

Model in woods wearing Thursday Captain

What makes them unique?

Service boots have their origins in the military. From the early-to-mid 20th century, servicemen around the world wore rugged, durable leather shoes. 

While military boots have changed over the years (see our list of Combat boots), the style has been adapted into the modern man’s wardrobe.

I recommend every guy gets himself a pair of service boots—they’re rugged and durable, but there are plenty of brands blending in a taste of class, too.

When should you wear them?

Service boots are casual, but they’re not for trudging around in the mud. 

One of the most iconic service boots is the Red Wing Iron Ranger. These look fantastic with a worn-in pair of raw denim jeans, but their easy-patina leather and nickel-plated eyelets have trouble fitting in with any other pant. 

However, new brands like Thursday Boots slim the silhouette and add a touch of sophistication to the style with their Captain boot. While it still doesn’t work with a suit, you can work them into a smart casual outfit. 

Thursday Boots Captain

The Thursday Boots Captain is an excellent deal. Made with Horween leather tanned in Chicago, these boots still look great after a year of harsh wearing. When (if?) these ever wear out, I’ll be getting them again.

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Our Top Picks:

Hiking Boots

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What makes them unique?

Hiking boots are built with support, durability, and water-resistance in mind. I’m sure hiking boot makers consider aesthetics, but these aren’t really for style. 

Modern hiking boots incorporate new materials invented to withstand extreme conditions. You’re less likely to find good old fashion leather uppers with steel shanks, and more likely to find rip-stop nylon and super-hardened composites. 

When should you wear them?

Well, when you’re hiking. 

I use a pair of hiking boots when I go camping. Good pairs are water-resistant, too, so I can take them with me fishing and I don’t have to worry about damaging them or getting my feet wet.

The Timberlands in our top picks could be worn for style if you’re looking to push the boundaries, but our other picks stick to function. 

Our Top Picks:

Derby Boots

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What makes them unique?

Derbys and Oxfords are often mistaken, but there’s a critical difference. 

The Derby has an open-lacing system, with eyelets sewn into the vamp. When it comes to boots, this makes a Derby much easier to slip on

When should you wear them?

There are several different styles that range from casual (and a little punk-rock looking) to dressy. While the open lacing system keeps these designated to the casual realm, they’re a great way to class up your everyday wear. 

Our Top Picks:

Oxford Boots

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What makes them unique?

Unlike Derby boots, Oxford boots have a closed lacing system. They’re a little harder to slip on, but they have more style versatility. 

While Oxfords are common in the business-world, the boot-style counterpart is much less popular.

These are one of the few boots that pairs naturally with a suit. 

When should you wear them?

Oxford boots are really best in the fall and winter, and look excellent paired in a smart-casual outfit or with a suit. 

Our Top Picks:

Work Boots

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What makes them unique?

A good pair of work boots are made to last for decades. They should have a sturdy grip and a high-quality sole.

Many work boots come with a steel or composite toe. 

Personally, when choosing a work boot, I prefer a composite toe. Unless you’re working in a dangerous environment that demands steel, a composite toe can withstand some hefty impacts, but it’s significantly lighter. 

Either way, make sure you get a hardened toe. Work boots should last for years and years, so investing an extra few bucks for the best of the best will pay off. 

When should you wear them?

Wear them out working (surprise!). Work boots are versatile enough to take camping and fishing, though they’re a bit too heavy for hiking. 

Any time you plan to kick up dust and get your hands dirty, you’ll want a solid pair of work boots with you. 

Our Top Picks:

Cowboy Boots

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What makes them unique?

These iconic boots are beloved by cow-pokes and wranglers out west. It’s common in California (where I’m from) to see folks dressed up in their best cowboy boots for Sunday service. 

A good cowboy boot is as sturdy as a work boot—that’s essentially what it is.

When should you wear them?

The most appropriate time for Cowboy boots is when you’re working. A rugged work-wear look is the preferred style for some folks, but you can style up the lower-ankle versions by pairing them with a crisp pair of jeans and a tucked button-down.

Cowboy boots are right at home with early morning farm work. 

Our Top Picks:

Moc Toe Boots

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What makes them unique?

Moc toe boots blend the water-resistance and sturdy build of a mocassin with the lining, sole, and ankle support of a work boot. 

They’ve come into fashion over the past few decades as a less-bulky work boot. Like the combat and service boot, moc toe boots occupy a middle space between fashion and function. 

When should you wear them?

Moc toe boots are a top-choice for fall and winter. The workwear aesthetic works well with jeans, but the mocassin top lends a refinement that plays well with chinos, too. 

Our Top Picks:

Jodhpur Boots

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What makes them unique?

Jodhpur boots are often seen as a unique alternative to the Chelsea boot. They have the same sleek silhouette as a Chelsea, but they have a strap and buckle that comes around the ankle. 

Originally worn by Polo players, they were popular with the social elites of the late 1800’s

These days they have wider appeal , and I’m not complaining. 

When should you wear them?

Any time you’d wear a Chelsea boot, a Jodhpur would be a good substitute. As far as the silhouette goes, they pair with jeans, chinos, and suits. The buckle adds intrigue the Chelsea doesn’t have, but some may find it unnecessarily showy.

Jodhpur’s are excellent fall and winter boots, and can take a casual outfit up a notch or five. 

Our Top Picks:

Engineer Boots

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What makes them unique?

Engineer boots are another rugged style of work boot, though they’ve been relegated to the fashion landscape for decades. 

The style is beloved by motorcyclists because of its no-frills simplicity and durability. 

Typically, an engineer boot is sewn from just a few pieces of leather and has a leather strap running around the ankle (and sometimes around the calf, too). 

Like the Jodhpur boot, while there once was a utilitarian purpose for the added hardware on the engineer boot, now it’s mainly for style. 

When should you wear them?

Wear engineer boots whenever you want to look like a total badass when riding a motorcycle. That’s really the best time. 

Our Top Picks:

Combat Boots

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What makes them unique?

Big and bold, combat boots are a fashion statement. Originally, combat boots were meant for—you guessed it—combat.

But in the ‘80s and ‘90s, combat boots became essentials in punk-rock style, and they’re now feeding into mainstream fashion. 

When should you wear them?

Combat boots make an excellent alternative to work boots, and you can find styles that are a little more fashionable—though if rugged, workwear style isn’t your thing, you’re better off looking elsewhere.

Dr. Marten’s has a few styles that look cool if you’re pushing the boundaries of fashion and style. On the other end of the spectrum, there’s the Garmont T8 Tactical boot—a literal combat boot used by the US Army. Not very stylish, but excellent outdoors. 

Our Top Picks:

Duck Boots

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What makes them unique?

Duck boots are the penultimate rainy day footwear for men. Built to be watertight through the sole and upper, these boots make a substantial addition to your collection if you live in a rainy climate. They combine a rubber work boot sole with a more casual leather upper.

Fun fact: Duck boots are also known as Bean boots as they were first created by the L.L. Bean company to keep hunter’s feet dry. 

When should you wear them?

These are amazing boots for rainy and snowy days. They have excellent grip so you have more traction, and they’re weather-proof so you don’t have to waltz around with wet socks. 

True to their purpose, Duck boots also make for good hunting/outdoorsman boots, though they can be too hot to wear if you’re treading in warmer months. 

Our Top Picks:

Balmoral Boots

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What makes them unique?

Balmoral boots are one of the few dress-boot options men have. They’re very similar to Oxford shoes in that they feature a closed-lace system, but the added height makes them a boot. 

When should you wear them?

You can wear Balmoral boots to the office if you wear a suit and tie, as they really shine in more formal attire. They’re a little too dressy to pair with jeans or chinos.

If you’re aiming for a formal look, I recommend choosing a high-polish black pair.

Our Top Picks:

Mukluk Boots

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What makes them unique?

Mukluks are ideal in below-freezing conditions. If you like to play in the snow, or if your work has you familiar with early morning frost, Mukluks will keep your feet dry and warm. 

When should you wear them?

I consider Mukluk boots to be closer to the workwear realm, though they’re also appropriate for ski trips. They’re a little bulky to fit into a modern man’s stylish wardrobe, though options like the Minnetonka Two-Button Hardsole are unique and could make for a great camping shoe.

Our Top Picks:

Which Boots Should You Get?

Quite the list, right?

Well, if you’re just getting started on your boot journey or you’re a seasoned expert, here are the “must have” boots for men. 

If you have a single pair of boots, or *gasp* no boots, start by picking up a pair of Chelsea, Chukka, and Moc Toe boots. 

Further Reading: Chukka vs Chelsea: Which Boots Are Best For You?

All three work in casual outfits, while a slim, dark pair of Chelsea boots can venture into suit territory.

M.Gemi Dritto

M.Gemi's Italian-inspired Chelsea boot has a slim Blake-stitched profile for that full European flair. This richly textured boot is luxury quality but costs around half the price.

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Moc toe boots can stand in and take a beating where work boots would otherwise, but they still look stylish enough to wear out on a Friday night (if you take good care of them). 

Want to take your collection to the next level? Try picking up a Balmoral boot for when it’s time to get fancy and a Service boot for adding rugged charm to your weekend attire. 

And if you’re ready to ascend to the lofty ranks of boot wearing mastery, pick up a pair that are suitable for your favorite activities. If you’re a hiker, but you don’t have purpose-built hiking boots, I assure you they’ll be a game changer for you. If you’re a motorcyclist, why not invest in a killer pair of Engineer boots?

Take another look at some options on our list. Once you really get into boot collecting, you’ll find endless variations, each brand with its own spin on a classic style. 

That’s where the fun begins.

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