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 17 types of boots every guy needs to know about before they pick up their next pair.
To be clear, I think there are only a few boots that a man needs to build a versatile collection. I break them down in the video below:
But if you want to know all your options, keep reading.
Chelsea Boots
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.
My Top Picks:
The Chelsea boot evolved slowly, so there’s no single brand that really put them on the map. But here are a few brands that are doing the style justice today:
My Top Pick Chelsea Boot
Beckett Simonon Bolton
(Get 15% OFF with code Spy15)
While the multi-month wait time is a bummer, the Beckett Simonon Bolton is the best Chelsea boot on the market. You won’t find a full grain Italian calfskin Chelsea for under $300 elsewhere, and certainly not with this leather thickness.
Check Price
- Thursday Cavalier (read my review)
- R.M. Williams Comfort Craftsman (read my review)
Chukka Boots
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.
Further Reading
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.
My Top Picks:
Clarks made the most popular Chukka, the Desert Boot (read our review), but those are iconic enough to deserve their own section.
Here’s my favorite chukka right now:
My Favorite Chukka
Thursday Scout
The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a stitchdown construction, this boot is hard to beat for value.
Check PriceRead Our Review
Desert Boots
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.
My Top Picks:
Clarks Desert Boot
The highlight of the Clarks Desert boot is the richly oiled pull up leather and the simplicity of its construction. While the crepe sole is delicate, it provides a lot of cushion, though you’ll need to give these boots a rest every so often.
Check PriceRead Our Review
- Velasca Umbrelee
Service Boots
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.
Further Reading
7 Best Service Boots Broken Down by BudgetI’m sharing the best service boots you can get and I’m breaking it down into different budget tiers so you can get exactly what you want for the right price.
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 theRed 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.
Red Wing Iron Ranger
If you survive the break-in period, the Iron Ranger will reward you with a rugged, manly boot that can last for decades with minimal care.
Check PriceRead Our Review
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 Captain
The Thursday Captain is an excellent deal. Made with Thursday's Chrome leather from Le Farc tannery (often compared to Horween Chromexcel), these boots are still holding up well after five years of wear. When (if?) these ever wear out, I’ll be getting them again.
Check PriceRead Our Review
More Great Picks:
- Wolverine 1000 Mile (read our review)
- Golden Fox Boondocker (read our review)
Hiking Boots
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.
My Top Picks:
Velasca Resegott
The Velasca Resegott is an outstanding boot and the price is very fair for the quality. The double-stitched stitchdown construction, heavy Vibram lug sole, oiled suede, and fully gusseted tongue make for a virtually waterproof boot that looks great and can tackle tough terrain.
Check PriceRead Our Review
Derby Boots
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.
My Top Picks:
Velasca Tencin
The imperfections of the tumbled kudu leather on the Velasca Tencin really pops to give this classy derby boot a lot of character.
Check Price
Oxford Boots
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:
Exclusive Discount Available
Taft Jack Boot
(15% OFF with code BOOTSPY15)
Either the Taft Jack Boot speaks to you, or it doesn’t. The material quality is excellent, and the construction is on par with what you’d find in any high-quality dress boot. But with such a distinctive boot, it’s awesome as part of a collection, though it’s not quite your “everyday” stomper.
Check PriceRead Our Review
- Beckett Simonon Nolan Brogue Boot
Work Boots
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.
Further Reading
6 Best Pull On Work Boots: These Boots Ain’t for DancingYou’re a working man and you don’t have time for lace-ups. We’ve got you. These are the best pull-on work boots for men in 2020. Pull ’em on and get it done.
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.
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Any time you plan to kick up dust and get your hands dirty, you’ll want a solid pair of work boots with you.
My Top Picks:
Ariat WorkHog
Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.
Check PriceRead Our Review
Cowboy Boots
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.
Further Reading
Our Top Picks:
Tecovas Cartwright
Made with beautiful full grain leather, this boot is a stunner. And it's built with classic boot-making techniques so it'll last you many, many years.
Check PriceRead Our Review
- Tecovas The Earl
- Ariat Workhog
Moc Toe Boots
What Makes Them Unique?
Moc toe boots are a style inspired by Native American moccasins. Their signature look comes from a U-shaped seam on the toe box.
These boots blend the water-resistance and sturdy build of a moccasin 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.
Grant Stone Brass Boot
The Grant Stone Brass boot is a total beast. The construction and stitching is meticulous and the build quality is the best I’ve experienced. While I personally prefer a slightly slimmer style, there’s no denying that the Grant Stone Brass Boot is one of the best value-offers in boots today.
Check PriceRead Our Review
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 moccasin top lends a refinement that plays well with chinos, too.
Our Top Picks:
Red Wing Classic Moc
The Red Wing Classic Moc Toe boot has quite a large toe box, which can be off-putting for some, though it’s an ideal match for American Heritage workwear aesthetic. The Puritan Triple stitching, 360-degree Goodyear welt, and thick full grain leather footbed all make for a beast of a boot that will easily last years.
Check PriceRead Our Review
- Thursday Boots Diplomat (read my review)
- Grant Stone Brass Boot (read my review)
Jodhpur Boots
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.
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.
My Top Picks:
Exclusive Discount Available
Beckett Simonon Douglas Jodhpur
(Get 15% OFF with code Spy15)
Made with buttery-smooth full grain Italian leather, the Douglas Jodhpur from Beckett Simonon is a substantial and stylish boot.
Check PriceRead Our Review
- Velasca Armiro
- Taft Dylan
Combat Boots
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.
My Top Picks:
Thursday Explorer
The Thursday Explorer is the coolest version of a combat boot I’ve seen. On the plus side, it’s rugged, durable, recraftable, sleek, and fairly lightweight for a heavy-duty boot. On the downside, it takes an outrageously long time to put on.
Check PriceRead Our Review
- Dr. Marten 1460 (read our review)
Duck Boots
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:
Sperry Avenue Duck Boot
Whether braving cold city streets or freezing sea air, the Avenue Duck Boot from Sperry Top-Sider keeps you steady on your feet (and keeps your feet toasty warm). The upper is made of a leather shaft and rubber foot, with Waterproof construction to keep out the wet elements
Engineer Boots
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:
Balmoral Boots
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 that extends above the ankle 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 unless you opt for suede as with the Velascas below.
If you’re aiming for a formal look, I recommend choosing a high-polish black pair.
My Top Picks:
Exclusive Discount Available
Beckett Simonon Elliot Balmoral Boot
(Get 15% OFF with code Spy15)
Made with buttery smooth full grain Italian leather, the Elliot Balmoral boot offers a restrained brogue pattern and a formal closed lace construction.
Check PriceRead Our Review
- Velasca Cheetah
- Allen Edmonds Hamilton
Mukluk Boots
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.
My Top Picks:
Harness Boots
What Makes Them Unique?
Harness boots are an ultimate rock and roll statement. If you’re going with these boots, you’re putting off a certain vibe.
This type of boot is a take on a western style, but it’s been adopted by moto culture and rock’n’roll. I think of Harness boots as a blend between an engineer and a Chelsea.
Why You Should Wear Them
You should wear a harness boot because its cool. These boots are typically easy to slip on and they have an “effortlessly awesome” feel to them. Not everyone can pull the look off, but if you can, you better give it a shot.
Our Top Picks:
Thursday Harness
Handmade by expert artisans in Portugal, the Harness Boot offers a uniquely sophisticated spin on the classic plain toe silhouette with just the right amount of attitude.
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- Frye Harness (read my review)
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?Both chukka boots and Chelsea boots are year-round styles, but what’s the big difference? Is one the better pick? Find out which is the best choice for you.
All three work in casual outfits, while a slim, dark pair of Chelsea boots can venture into suit territory.
Velasca Magut
A pair of dark brown suede Chelseas should be in every man's closet for their versatility alone. These are blake stitched for maximum sleekness with high quality suede calf leather. What I love about Velasca is you can choose your sole for each style---pick from Vibram or Dockers rubber (most versatile and better for winter) or leather (most dressy).
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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.
Velasca Ofele
With suede calfskin leather, the Velasca Ofele is my top pick for a suede Chelsea boot. The knap is finer, the leather is sturdier, and the overall construction and style are well worth the cost.
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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.
Looking for something more seasonally specific? Check out my YouTube guide to the best boots right now:
