Boot Camp: The Essential Men's Dress Boot Guide

If you are on the hunt for a stylish pair of boots that can be dressed up or down than the dress boot is for you. Dress boots are sleek, versatile and the perfect addition to any guy’s footwear rotation. In this Boot Camp guide we are going to introduce the six most common types of men’s dress boots and follow up with a short guide for those shopping for their very first pair. 

Boot Camp: Guide to mens dress boots

What is a dress boot?

Dress boots are a style of boot that can be worn with suits, business casual outfits and a nice pair of slacks without looking too informal. Unlike most casual boots, a quality pair of dress boots can make jeans look more refined and won’t look out of place in the office. This versatility is what sets a dress boot apart from a strictly casual or chunky winter boot. The lasts are more formal, the leather is finer, and the soles resemble those of dress shoes.

Dress Boots vs Dress Shoes

Why upgrade to a pair of dress boots when dress shoes will do just fine? Men’s dress boots are great for guys who want something different, stylish, and comfortable. Because dress shoes are usually the norm, wearing a sleek pair of dress boots will elevate your style and even earn you compliments.

Dress boots can also provide ankle support and comfort that is usually lacking in dress shoes. For those living in colder climates, dress boots can be purchased with reinforced outsoles and lining to provide extra protection in cold weather. 

Types of Men's Dress Boots

1. Anthony Veer Texas Dress Boot ( Amazon )  2. Meermin Dark Brown Calf Derby Boot ( Meermin )

1. Anthony Veer Texas Dress Boot (Amazon)

2. Meermin Dark Brown Calf Derby Boot (Meermin)

1. Balmoral Boots (Oxford Boots)

Balmoral boots are the most formal men’s boot style and one of the only type of boot that can be paired with a formal suit. This is because balmoral boots share a lot similarities with oxford dress shoes. Balmoral boots are defined by their closed lacing system that gives them a more formal style over their lace-up boot counterparts. Because the closed lacing system creates a vertical visual divide in the uppers, it allows balmoral boots to look like traditional oxford dress shoes at a quick glance. Other features that define a balmoral are low heels, rounded toes and thin dressy soles that normally made out of leather. 

2. Lace-Up Dress Boots

The lace-up boot is probably what many imagine when they think of men’s dress boots. Unlike balmoral boots, lace-up boots feature an open lace system and more casual styled uppers. If a balmoral boot is like the oxford of boots, then a lace-up dress boot is like a derby or blucher with a longer shaft. Although lace-up boots can easily be paired with a casual suit, they are rarely appropriate in very formal settings where strict style conventions still apply. However, lace-up dress boots are as versatile as they come. They can be dressed up or down with relative ease and look great with everything from casual denim to smart outfits at the office.

3. Thursday Boot Co. Duke Chelsea Boots ( Amazon )  4. Southern Gents Emerson Jodhpur Boots ( Amazon )

3. Thursday Boot Co. Duke Chelsea Boots (Amazon)

4. Southern Gents Emerson Jodhpur Boots (Amazon)

3. Chelsea Boots

Chelsea boots are a great dress boot option because of their close tapered fit. What’s great about chelsea boots is that the lack of laces allows for a sleek silhouette that prevents the bulkiness that plague many lace-up boots. Although chelsea boots may be too causal to wear with formal suits, they go great with slim-fitting pants and can look sharp when paired with a dress shirt and sports coat.

The key to dressing up chelsea boots is to pay attention to the boot’s fit and materials. Avoid bulky styles and instead opt-in for a close fitting chelsea boot that tapers nicely to the foot and ankle. Unless you are going for a more casual look, avoid suede chelsea boots for your first pair as suede is considered a more casual leather. Instead stick with a high quality black or brown leather upper for a more polished look. 

4. Jodhpur Boots

Jodhpur boots are very similar to a chelsea boot but has enough distinct differences to be considered a class all of their own. The first thing you’ll notice, is that just like the chelsea boot, jodhpur boots lacks any laces. Instead the boot is secured around the ankle by a single strap and buckle. This gives jodhpur boots a formal edge over the chelsea’s elastic side strap and helps give the jodhpur a more refined look.

Today, jodhpur boots are less popular than other ankle boot styles such as the chelsea and chukka boot. But jodhpur boots can look quite distinguished when paired with casual suits or denim and shouldn’t be counted out as a dress boot option. Because jodhpur boots have very little embellishments, the look is very sleek and elegant. The single strap allows for a stylish edginess that looks quite refined as a dress boot. 

4. Paul Evans Heston Monk Strap Boots ( Amazon )  5. To Boot New York Derby Chukka Boot ( Amazon )

4. Paul Evans Heston Monk Strap Boots (Amazon)

5. To Boot New York Derby Chukka Boot (Amazon)

5. Monk Strap Boots

Monk strap boots are defined by one or two straps that secure the foot instead of traditional laces. Like the chelsea, monk strap boots are an edgier choice but their lack of exposed lacing and handsome silhouette makes it very easy to dress up. When it comes to their shoe versions, monk strap shoes are considered an intermediate shoe that fall somewhere between an oxford and a derby dress shoe. Their big brother, the monk strap boot, also plays by the same rules. It’s not exactly formal but a nicely fitting monk strap boot is extremely versatile and can be worn with just about anything less formal than a suit or tux. 

When it comes to shopping for a monk strap dress boot, the same guidelines apply as any other dress boot. Stick to dressier leathers and soles on a refined last. Avoid anything too ornate for your first pair of monk strap boots. Stick to a classic calf-skin leather and play it safe with colors by going with black, brown or oxblood for your first pair. Another detail to pay attention to is the color, size and shape of the buckle. Avoid flamboyant buckles that are too trendy and quick to go out of style. 

6. Chukka Boots

Chukka boots can be defined by their two or or three eyelets, open lacing, and a shaft that reaches the ankle. Out of all the boots on our men’s dress boot list chukka boots are probably the least formal. The key to dressing up a chukka boot is fit and materials. You want your chukka boot to fit snugly around the ankles so that it does not leave an ugly silhouette when worn with pants. Avoid suede if possible and instead go for a classic brown leather. Chukka boots can easily look like a casual shoe so it’s important to be mindful of the small details.

Chukka dress boots should not be confused with the popular desert boot style that uses thicker crepe or rubber soles. There is a big difference between a dress chukka boot and a Clark’s Desert boot which is strictly casual.

Shopping for your first pair of dress boots

Every guy is different and it’s really important that you note where and when you’ll be wearing your dress boots the most.  Do you need boots for work? Is the environment formal business suits or business casual? Do you need dress boots that can handle bad weather? Or will leather soles do just fine? The formality of the boots you choose will really depend on your needs and lifestyle.

Here are some guidelines for those who are shopping for their first pair of dress boots. You don’t have to follow this guide to the note, but it will help you avoid choosing a boot style that is too casual. As with anything else, you should play it by ear and decide for yourself how much informality you can get away with. 


Ideally you want your dress boots to fit closer to the foot with a round toe. This means no chunky insulated winter boots. And no odd shaped toes or soles. Keep it classic and sleek.

Leather and suede dress boots: Bexley Irving Gomme Country Boots ( Bexley )

Leather and suede dress boots: Bexley Irving Gomme Country Boots (Bexley)


Dress boots really shine when they are made of finer leathers. The general rule here is that the finer the leather, the more formal your dress boots will be. Stick to a high quality calfskin or leathers that can provide a bit of a shine. If you want to learn more about leather than check out our leather guide

When shopping for your first pair of dress boots keep your leather colors simple and versatile. Stick to black for a more formal look. Or step it down with dark and light brown, oxblood or burgundy. Suede is considered a casual leather so avoid it if you want to maximize your boot’s formality. Hold off on purchasing dress boots in daring colors and materials until you have owned a basic pair.

Dainite soles: Thursday Boot Co. Dress Chukka Boots ( Amazon )

Dainite soles: Thursday Boot Co. Dress Chukka Boots (Amazon)


Soles are very important as they can dictate how dressy the boots appear. With dress boots, you want to stick to slim dressy soles. The two most common types of soles in dress boots are going to be leather soles and dainite soles. Dainite soles are low profile enough to give your boots a sleeker look while still providing great traction in bad weather. 

Avoid chunky soles when shopping for dress boots. Thick lugged soles are casual in nature and should be reserved for winter and work boots. If you would like to learn more about soles then make sure to read our guide to boot soles.

Broguing gives a more casual look:  Allen Edmonds  Dalton Boot ( Amazon )

Broguing gives a more casual look: Allen Edmonds Dalton Boot (Amazon)

To brogue or not To Brogue?

When shopping for dress boots you will come across brogue boots and styles that feature embellishments. Usually the more broguing a boot has, the more informal it becomes. You are going to want to play this by ear and figure out how much informality you can get away with, especially if you plan on wearing your dress boots in an environment with a stricter formal dress code. To learn more about brogue boots and other toe styles makes sure to check out our boot toe guide.

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