An Effortless Guide (15 Popular Styles!)

It’s easy to be overwhelmed by the dozens of types of boots available for men today. But with just a little help from this guide, you’ll be able to find the right type that effortlessly matches your own personal style.

In this guide, we’ve focused on the types of boots that the average guy might encounter and be interested in wearing. Our apologies to any sailors, equestrians, or jungle explorers out there reading this.

You’ll find everything from casual to dressy, work tough to plush and comfy, and boots of every height, among the dozen plus styles highlighted. After a brief origin story or description of the boot, we’ll give recommendations for brands and specific models we especially like.

So, let’s get started, shall we?

 

Chelsea Boot

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Close-fitting and ankle high, Chelsea boots are always made with an elastic side panel. They’re one of the few long-standing items of Victorian-era fashion, and made a big comeback in the 1960s thanks to The Beatles.

The Legend from Thursday Boot Co. is an awesome choice for a Chelsea boot, thanks to its combination of comfort and durability. They’re an incredible value for what you get, with glove leather interiors and Goodyear welt construction.

And if you’re still experimenting with the Chelsea and are looking for a solid budget option, we recommend the New Republic Sonoma. See our full review on the Sonoma suede Cheslea.

Ankle Boot

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Inspired by the Chelsea boot, ankle boots share the snug and form-fitting qualities of their predecessors. Instead of elastic mesh, ankle boots feature a zipper or strap that won’t stretch out over time; be advised that men with wider ankles or more muscular calves may find this less comfortable.

Ankle boots are definitely a less common style than Chelseas, so finding quality pairs may take a little more digging. We’ve had good luck with Beckett Simonon boots in the past, and their Easton side zip ankle boots are a great option.

Chukka Boot

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The story goes that Chukka boots may have received their name from polo, where a single period of play is sometimes known as a chukka.

Ankle high and most commonly made with leather uppers and crepe soles, they’re an open lace boot style that can look great with jeans and chinos alike.

Astorflex makes an awesome Chukka boot, the Greenflex. And of course you can’t go wrong with the always-recommended Clarks Desert Boot.

Wingtip Boot

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Classy but not quite formal dress.

Wingtip boots are great for embellishing a casual outfit or keeping a dressier fit from going overboard.

They’re immediately noticeable by the intricate detailing on the boot tips, and look especially nice when given a polish and shine.

A great pair of wingtips will set you back a fair bit, with high-quality examples starting at around $300. Velasca’s Sciostree consistently gets rave reviews for its quality relative to the price. Plus, the Vibram soles are easy to have replaced if they wear out!

Dress Boot

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Built like dress shoes but made to cover the ankle, dress boots are the go-to choice to match with formal wear. Many styles are referred to as dress boots these days, but lace-up cap toe boots with closed lacing are the real deal.

Beckett Simonon’s Elliot Balmoral boots are a good example of this style. Pair these up with formal trousers and sportcoats or suits, especially in the colder months.

Jodhpur Boot

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Another variation of the ever-popular Chelsea boot, Jodhpur boots are ankle boots that were originally designed for horseback riding. They feature a rounded toe, low heel, and a strap that usually wraps around the entire ankle.

Fun fact: Jodhpur boots originated in India, and are named after the town where local polo riders popularized them. Beckett Simonon makes an absolutely gorgeous pair of Jodhpur boots with clean lines and ultra-soft leather.

Hiking Boot

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Perhaps the broadest of all men’s boot categories, the many stylistic variations of hiking boots could likely fill an article of their own.

We especially appreciate hiking boots that can double for casual wear, since many of the top-end hiking boot features are geared more towards dedicated hiking enthusiasts.

A classic example of this comes from Danner, with their Mountain Light boot style that originally debuted in 1979. One piece leather uppers, Vibram outsoles, and stitchdown construction that can be fully recrafted make them a solid all-round choice.

Hunting Boot

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Not planning on bagging an elk come next hunting season? No problem. Hunting boots can make their way into your wardrobe, as they’re a wintertime staple for casual wear in much of the Northeast.

We love their waterproof construction and that the traction-heavy soles let them double as snow boots.

Irish Setter’s Wingshooter boots have achieved a cult status among select groups of hunters. They’re surprisingly affordable, and come in a wide variety of ankle heights and styles.

Work Boot

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Designed for getting things done, work boots feature some of the most heavy duty construction of any boot style.

A number of specialized styles may be generally referred to as work boots. The ones we have in mind feature waterproof construction, thick and heavy soles, and breathable linings that keep them comfortable throughout the day.

You’re spoiled for options with work boots, but Red Wing’s Iron Ranger might be the most recognizable in this style. It’s a modern classic that’s kept a devoted fan base for years.

Rain Boot

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Also known as Wellington boots, gumboots, or galoshes, rain boots don’t just come in yellow and kids sizes. There are plenty of waterproof boot options available, but rain boots have a distinctive style that’s impossible to miss.

Hunter’s Original Rain Boots are the genuine article, and have stood the test of time since their introduction in 1956. They’re insulated for winter wear, and 100% waterproof from top to bottom.

Snow Boot

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When it gets really cold outside, nothing short of a fully insulated and waterproof boot will do. Snow boots excel in wet, snowy, or icy conditions, and come with exteriors that are easy to clean.

The tradeoff is that snow boots tend to be heavier and less breathable than other cold weather boots.

L.L. Bean’s Shearling-Lined Bean Boots are about as warm as it gets for snow boots. Better yet? They are still made stateside at their factory in Maine.

Trench Boot

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Low profile and inspired by military classics, today’s trench boots feature a slightly taller heel and generous lacing.

Fit wise, they fall somewhere between a Chukka and a hiking boot. These boots go great with casual or smart casual outfits!

Taylor Stitch’s Trench Boot is a prime example of this style. Handmade in Mexico with Goodyear welt construction, they’re fully resoleable and lined with soft sheepskin leather for a butter-smooth fit.

Combat Boot

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The same sort of boots worn by our enlisted military, combat boots prioritize function over form. They provide an excellent combination of grip, stabilization, and protection.

Plus, they enjoy a niche popularity that’s continuing to grow amongst counterculture groups.

Dr. Martens (or Doc Martens, or simply “Docs”) pay homage to that instantly recognizable style. These are the 1490 model, loosely based on the classic combat boot.

Cowboy Boot

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Underslung and slightly higher heels, round or pointed toes, and no lacing: Cowboy boots are a style entirely unto themselves. Cowboy boots are usually made from cowhide leather and are sometimes decorated.

You’ll also see cowboy boots made from a plethora of exotic animal skins like buffalo, snake, and alligator. The heel heights themselves also differ, depending on if you’re mostly walking in them, or riding, etc.

Originally designed for the specifics of day-long work on horseback, they have smooth soles and can take a long time to break in properly.

Tecovas’ Cartwright Cowboy Boots are handmade in the traditional style, with modern embellishments of toe stitching and hand-corded patterns on the shaft.

Engineer Boot

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One of the few types of boots to originate in America, engineer boots have a tall, laceless design and exceptionally durable construction. You may recognize them more for their adoption by motorcyclists, which led to their “tough guy” image.

Frye’s Engineer 12R strikes a great compromise between rugged style and accessibility, and we think they would look great with a pair of bootcut jeans in a casual outfit.

Which Are the Best Types of Boots for Men? Well, that depends!

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Now that you’ve seen the types of boots available to you, which one are you thinking might best suit your own personal style?

We recommend considering two things in particular before deciding:

• First, how dressy are the outfits you plan on wearing your boots with?
• And second, in which seasons will you be wearing the boots?

Once you’ve narrowed that down, you can refer back to this list of styles to point yourself in the direction of a quality brand.

If you want something for everyday wear, you can’t go wrong with a chukka, Chelsea, or trench boot, for starters.

Got any specific questions? Feel free to DM me on Instagram.