If you’ve spent as much time as I have obsessing over men’s boots, you might have noticed that at fist glance, there seem to be about a zillion boot styles for men.
(I’m not going to say exactly how much time I spend thinking about boots, but it’s an amount my wife has accurately described as “embarrassing.”)
See, each year, usually starting in the fall, menswear stores and brands roll out a ton of new releases, new colors and allegedly new styles of boots for guys to choose from.
But when you look closely at the new releases, it doesn’t take long before a clear pattern starts to emerge: this year’s must-have boots look suspiciously similar to last year’s. And the year before that. And the decade before that.
That’s because, while it may seem like there are a zillion men’s boots on the market, the truth is that there are really only a few fundamental men’s boot styles.
And once you know which styles will stand the test of time and make you look your best for years to come, choosing the right pair becomes easy.
In this post I’ll lay out nine of the sharpest, most classic boot styles for men, explain how you can get the most out of each style, and provide a few examples of which ones to buy if you want to (corny pun alert!) step up your boot game (you were warned).
The Sharpest Men’s Boots Styles
Rounding Up the Best Men’s Boots for Everyday Wear
Cap Toe Boots
If the handsome devil is in the details (which he most certainly is), then cap toe boots just might be the most wickedly handsome men’s boots types available.
Some would argue that a cap toe isn’t so much a style of boot as a stylish add-on to other boot styles, and technically they’re right. (You can, after all, find cap toed versions of most of the boot styles listed below.)
But cap toes offer such a distinct and dapper look that, for my money, they deserve their own place on this list.
Whether you’re wearing sleek dress boots with a suit or chunky combat boots with jeans, pair a cap toe with a well shaped toe, and you’ve got a pair of boots that will look sharp in any situation.
A Couple Cap Toe Boots Try:
Sometimes the most stylish option is also the simplest. (Actually, scratch that. Most of the time the most stylish option is also the simplest.)
And chukkas are not only as simple, sleek and stylish as it gets, they’re also one of the most versatile boot styles on this list.
A sleek pair of leather chukkas works well with even the most formal suit, while a crepe-soled pair of suede chukkas is the preferred casual boot of style icons like Steve McQueen and Daniel Craig’s 007. (But don’t worry: they look just as good on guys who don’t happen to be blonde, fit and roguishly handsome.)
A Couple Chukkas to Try:
Combat boots evoke the rugged style of WWII-era commandoes, without requiring you to wear the (also cool, but impossible to wear in real life) WWII era helmet.
A distinctly casual style, combat boots make for a perfect option in pretty much any situation where you would wear denim and a chunky type of sweater.
Fortunately, in the increasingly casual world we live in, situations like that are more and more common place, which makes combat boots a more versatile option than you might think.
As mentioned above, you can get most boots in a cap toe style, but I find combat boots in particular benefit from the cap. Combat boots tend to have a more rounded toe shape (as opposed to the sleeker toes of the chukkas featured above, for example), and the cap toe provides a stylish element that helps elevate an otherwise super casual look.
A Couple Combat Boots to Try:
Chelsea boots are named after comedian and former Brooklyn Nine-Nine star Chelsea Peretti, who invented them in between shooting seasons 2 and 3 of the show.
Just kidding. (The irony here is that Chelsea Peretti is a hilarious comedian who would probably hate that lame joke.)
In truth, Chelseas get their name from the Chelsea Boot Company, whose origins date back to 19th century Victorian England. The Chelsea company originated the style of boot that’s since become synonymous with its name, which features an elastic section around the ankles that allow the boots to be slipped on and off easily.
Like cap toes, Chelseas can be found in various style (I personally have a pair of wingtip suede Chelseas and a separate, sleeker pair of chocolate brown cap toe Chelseas), the classic version has a rounded toe and a thick sole that not only makes them great for any casual situation, but makes it super easy to slide them on and off.
A Couple Chelsea Boots to Try:
Wingtips, also known as brogues, offer a perfect middle ground between rugged and dapper.
Brogues originated with English hunting parties, who trenched through the muddy countryside in search of game. (The small holes in the leather allowed water to seep out rather than build up in their boots.)
Long a staple of men’s fall fashion, a well made pair of wingtip boots can stylishly carry you all the way through winter in most climates, particularly if you opt for a pair with a hearty rubber sole that can stand up to snow and ice.
But what’s great about brogues is that you don’t have to sacrifice style in the name of practicality. While classic English gentlemen would have been appalled to see brogues worn indoors, today many people would probably consider wingtips to be dress boots.
(Although, as you’ll read below, I am definitively not one of those people.)
A Couple Wingtip Boots to Try:
Another style of boot that’s admittedly a little vague, I define “dress boot” as any boot that as a sleek toe shape, clean lines, a thin sole and few extra details (which is why wingtip boots are excluded from this category, at least in my humble opinion).
Dress boots can easily be worn with a suit, but one of my favorite moves is to elevate an otherwise casual look by throwing on a sleek pair of dress boots. If everyone else is wearing sneakers, round-toe combat boots or Chelseas, a sleek pair of dress boots will help you make a stylish statement without feeling too peacocky.
One word of warning though: since a thin sole is one of the key criteria for dress boots, if you live in a colder climate then you should plan to wear them more in the fall and spring than in the winter.
A Couple Dress Boots to Try:
The Jodhpur boot doesn’t share its name with a comedian (at least not any that I’m aware of), but it does share its name with a city in India, where they originated in the 1920s.
Jodhpurs are distinguished by the high buckle at the top of the boot, which was originally used by polo players to cinch the boots around their ankles.
Today a lot of models just include the buckle for decoration and actually pull on much like Chelseas.
A Couple Jodhpur Boots to Try:
Moc Toe Boots
When it comes to men’s shoes and boots, toe shape is one of the most important factors in determining a pair’s stylishness (yes, that is so word!).
As a rule of thumb, I tend to favor a toe shape that’s somewhere between round and triangular. As a point of reference, the toe shape on both pairs of Beckett Simonon shoes that I reviewed awhile back is pretty much perfect.
But there are a few exceptions to the rule, the biggest of which is probably the moc toe boot, a classic casual staple that gives off a distinctly rough-and-tumble vibe.
Named for their resemblance to moccasins (note the stitching around the squared-off toe), moc toe boots both look and feel masculine, making them a perfect option for guys who want to inject their look with a little ruggedness.
A Couple Moc Toe Boots to Try:
And speaking of ruggedness, nothing says “work hard/play hard” quite like a pair of chunky, protective, thick-soled work boots.
Much like the denim/chambray shirt, which started as the preferred shirt of working men (and the requisite shirt of many prisoners) before being adopted by the fashionable white collar set, the work boot can be found on both the construction workers who build office towers and the laptop-wielding businessmen who work within them.
And it’s not hard to understand why. If you work on a construction site or in any industrial environment then the steel boot is probably mandatory. But even if you don’t, they’re perfect for yard work, shovelling snow, hiking (they’re designed for guys who stand all day, so they’re comfy as hell) and other household duties.
Whether you work hard at a physically demanding task or just want to look like you do, work boots are great to have on hand.
A Couple Work Boots to Try:
The Next Step Toward Sharp Style
“Step.” Get it? Like with your boots. (I’m the worst.)
Now that you’ve read the whole post (thanks for hanging in there, by the way), you’ve got a strong understanding of which which types of men’s boots you need to add to your wardrobe.
(And if you want even more footwear advice, you’ll definitely want to check out my post outlining the most stylish types of shoes for men.)
But while boots are an important facet of a man’s style, they’re really only one piece of the larger menswear puzzle.
If you really want to learn how look sharp and stand out, you need to know how to nail the details—all the details.
Fortunately, I’ve put together a checklist that will help you do just that. Enter your email address below and I’ll send you the Nine Details You Need to Nail to out-dress the other guys and put your best face forward.
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More Advice on Men’s Boots and Shoes from Irreverent Gent:
- 17 of the Best Men’s Chukka Boots Available on Amazon
- Johnston & Murphy Karnes Cap Toe Boot Review
- The (Absolute) Best Men’s Casual Shoes
- Stylish Boots in the Irreverent Gent Men’s Shop
More Men’s Boots Advice from Around the Web:
Banner image: Sarah Pflug via Burst
Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a (patient, if long-suffering) Toronto sports fan and the husband of a wonderful (and fortunately much more patient) wife.