A Guide To Men’s Boot Styles | Vionic

Are you looking for a guide to men’s boot styles to help guide your search for the perfect pair of boots? We’ve got you covered! We know that boots are a go-to style for inside the office and for out in the wilderness, which is why this multi-functional staple is an essential item for any well-rounded wardrobe. Depending on the style of boots you choose, you can channel a classic, clean-cut style, opt for a more rugged rebelliousness, or add a dose of sophistication to any look. We know it can be a challenge to wade through all of the information available to determine what the main boot styles are for men, what characteristics set them apart, and how to make sure you’re choosing classic men’s boots that will compliment your style and accurately reflect your aesthetic. That’s why we’ve taken the guesswork out and done the research for you so that you can rely on one easy-to-follow guide to men’s boot styles to help give you the information you need to make an informed decision about what style of boots best fits the stylish orthopedic shoe criteria you’re looking for while still giving you the style and support you need.


Not only do we want to educate you on the main men’s boots styles, but also make sure you’re choosing boots that will give you support and comfort over the long-term. We’ve earned a place in the industry as a trusted resource that has dedicated research teams, foot doctors, and shoe stylists to make sure you can have all of the support and comfort you’re looking for in the leading and wide selection of boot styles. Along the way, we’ll educate you on the top men’s boot styles, what sets each distinct style apart from the others, and what features you should be looking for in your boots to make sure they are long-lasting and supportive with every step.

Men’s Boot Styles (Made Simple!)

We know keeping up with the variety and wide range of styles and trends in men’s fashion can feel like a chore, but with our introductory guide, you’ll have the information you need to start your search for the perfect pair of men’s boots to add to your arsenal. Whether you’re looking for a pair of classic chukka boots or more mod Chelsea boots, we will give you the baseline knowledge you need to make an educated choice about what style will best fit your lifestyle and the types of environments in which you are hoping to wear your new, stylish boots. No matter what style you are looking for, men’s boots are a great addition to any wardrobe. Keep reading for a breakdown of the three main types of men’s boots styles you should be aware of and what distinct features set them apart from one another.

Chukka Boots

First up on our list are a classic must-have boot for your wardrobe: the chukka boot. You may be wondering how these boots got such a unique name. Some believe that chukka boots earned their unique moniker from the game of polo, during which there is a period of time called a chukka. Chukka boots gained widespread popularity after the Duke of Windsor wore a pair in 1924 and their popularity hasn’t waned in modern society. Chukka boots are a casual ankle boot that has short laces, often with only two to three eyelets that the laces fun through and often come in classic materials such as leather or suede. The beauty of chukka boots is their simplicity. With clean, modern lines, chukka boots are the perfect pairing for many different outfits ranging from casual to business casual. Dress the casual boots up with a suit to make a smart, memorable outfit or dress them down with jeans and a button down. No matter what they are paired with, chukka boots are beloved for their versatility and fashionable look. Chukka boots offer a unique dose of style to men’s wardrobes that have made them extremely popular. We recommend looking for chukka boots in neutral hues so that they pair well with everything in your closet and can be worn frequently in your footwear rotation.


If you are looking for a pair of perfect chukka boots to incorporate into your footwear arsenal, check out our Chase Chukka Boot. Available in neutral tones of leather or weather resistant suede, the Chase Chukka Boot will never go out of style. The Chase is a phenomenal all-occasion shoe that features a durable outsole, fine stitching details, and a two-tone heel to distinguish its unique style. With our innovative podiatrist-designed Orthaheel technology built-in, you’ll get the style of a classic chukka boot with superior orthotic relief, support, and stability to help maintain your natural alignments with every step.

Chelsea Boots

If you’re looking for a great pair of men’s pull on boots to add to your arsenal, Chelsea boots may be the perfect pair for you. Did you know that Chelsea boots actually have ties back to Victorian time? With its design and invention thought to trace back to J.Sparkes-Hall, the boot maker of Queen Victoria, the Chelsea boot has only further gained a place as one of the top boot styles in modern society. They gained their unique moniker when the popular crowd in London’s Chelsea started wearing them a century after Queen Victoria’s bootmaker first developed them. From there, their popularity skyrocketed with everyone from The Rolling Stones to The Beatles sporting Chelsea boots. Now that you know the history on these stylish boots, we want to want you through what distinguishes a Chelsea boot from other styles of boots.


If you’re wondering how to spot a Chelsea boot, we’ve got you covered. Chelsea boots often feature an upper that is made by joining together two pieces of leather, called a “vamp” (the front) and the “quarters” (the back). These pieces of leather are then sewn together and often feature a panel of elastic materials that joins the two pieces of leather together. A notable benefit of the Chelsea boot is their ability to be quickly slid on and off with minimal effort due to the piece of elastic joining the leather, making them perfect if you’re on the go and want to avoid fussing with laces. Another distinctive feature of Chelsea boots is that they will rise to an ankle-hitting height. This ankle-hitting height makes them extremely versatile and offers a more rugged edge than a traditional men’s dress shoes while also adding more class and style than sneakers. The other feature to look for in a Chelsea boot is the shape of the toe, which hits the perfect balance of taper to avoid being too pointy and formal, while also not being too bulbous and informal. Chelsea boots are a wear-with-everything staple that can change your style game and instantly elevate any outfit. Chelsea boots are now worn by both men and women alike with styles tailored to make any individual feel confident and stylish.


If you’re looking for the perfect pair of Chelsea boots to add to your footwear collection, take a look at our Kingsley Chelsea Boot. Think of the Kingsley Chelsea Boot as a classic Chelsea boot with a sleek makeover. The Kingsley is a style favorite that is made with twin gore panels that will give you the comfort, ease, and pull on goodness you’re looking for. With sophisticated detailing, this practical boot will have you looking poised and polished whether you opt for the buttery-soft brown leather, black leather, or dark taupe suede treated with a protective coating to help against inclement weather. With perfect ankle-high height and a durable rubber outsole, the Kingsley Chelsea Boot is the perfect companion for your next adventure.

The Wingtip Brogue Boot

Looking for a boot style that is the perfect blend of classic style and ruggedness? A wingtip brogue boot may be the boot you have been looking for. To understand what the wingtip brogue boot is, it’s important to take a look back in history for a moment. Let’s start with what brogue means and work our way to how that relates to what a wingtip is. A brogue is a term used to describe regional accents in the United Kingdom, particularly within the English West Country and Scotland. So how does this relate to shoes? Some believe that the brogue’s origins trace back to believing that the accent sounded as if they had “a shoe in their mouths.” The Irish word “brog” is also used to describe a “rough or stout shoe”. Now the terms brog or brogue are often used to describe a shoe. However, the meaning of brogue doesn’t stop there. To understand what the term brogue means for modern boots it’s important to understand what broguing is. Merriam-Webster dictionary defines broguing as “ornamentation of shoes employing heavy perforations and pinkings.” In today’s styles, brogue boots are boots that have distinctive perforations on them. Now that you’re an expert on what brogue means, let’s walk through how you can tell they are a wingtip boot.


You’ve probably heard of the term wingtip before, but do you know how to tell whether or not a shoe is a wingtip or not? Many people have heard this common shoe term but don’t know how to distinguish a wingtip boot from another type of boot. Don’t worry, we’re here to help make sure you always know what boots are a wingtip! If a boot is a wingtip boot, when you are looking from above, the cap of the shoe will have a pattern of perforations and stitching on it that will look like an “M” or a “W”, depending on your viewpoint. That shape will then extend along both sides, like “wings”, and often end near the ball of the foot. There are many different variations of the wingtip boot, but this will allow you to quickly spot them. Wingtip brogue boots are not only steeped in history, but they are also made to be functional and ornate, a combination that makes them add style to any outfit.


If you’re looking for a wingtip brogue boot that will give you style, check out our Wesley boot. The perfect boot for the rugged urbanite, the Westley has both craftsmanship and function to make it the perfect addition to your footwear wheelhouse. Made with a full grain leather upper, fine stitching detail, a functional inner side zipper, and an exposed wooden and rubber outsole, the Wesley is a wear-with-everything boot. The Wesley also has a lace-up front, which gives it a rugged, yet polished finish. With our Orthaheel Technology built-in, you’ll not only be stylish, but you will also be supported and comforted with every step.

Choosing the Right Supportive Features

When you’re looking for the perfect pair of men’s boots, choosing a style you love should be equally as important as making sure the boots have the right supportive features. Unfortunately, the fashion industry can turn a blind eye to comfort, while the foot health industry often doesn’t consider fashion. To make sure you’re getting the best of both worlds, we recommend looking for supportive features that will keep your feet comfortable with every step. Below are a few of the top supportive features you should be looking for.

  • Arch support that hugs your natural footprint
  • A footbed that is designed to promote your natural alignment from the ground up
  • A deep heel cup to help promote stability
  • A firm yet flexible midsole to help optimize your balance

Also, feel free to check read our related blog that lists the most comfortable men’s dress shoes.


At Vionic, we believe you should never have to choose between style and support and we’ve built our business around delivering fashion-forward footwear that has the latest biomechanic technology embedded to make sure you are comfortable and supported with every step. Vionic’s men’s boots are designed in the latest fashion-forward styles and engineered with Vio Motion support and technology that is biomechanically designed to hug your arches and optimize your support so that you never need to choose between support and style again.

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