How To Wear Men’s Boots: A Complete Guide

Boots are essential to every distinguished gentleman’s closet, making how to wear men’s boots a top style question. You probably have a pair or two in your closet, but styling them has been a bit of a mystery…until today. We have everything you need to know about boots and more, in your complete guide to wearing men’s boots.    

What is a Men’s Boot?

We can’t start a guide on how to wear men’s boots without first getting down to the sole of what a boot is. Let’s begin with a little style history, shall we? Boots were first constructed for the practical purpose of protection. From cold weather to battle, boots were created for greater coverage than a traditional shoe or sandal. What we now know as a boot started off as a thick cover for the foot and the ankle. Originally consisting of a lower shoe and separate leg covering, over time the pieces were joined together into a single piece. This footwear phenomenon has since evolved into a style icon of many different types, heights and styles.

How Should Men’s Boots Fit?

Right behind the question of how to wear men’s boots is how should men’s boots fit? There are many ways to find the right fitting boot for you, starting with size.


It seems like a no-brainer, but size is the most important aspect of fit. We are so connected to the size we think we are, that we sometimes wear a selection that is not right for us. Size varies among brands, so trying a pair on for comfort instead of staying true to size is key. Wearing a boot that is too big or too small can cause friction. This abrasion can create structural problems like bunions or hammer toes. Give your boots the boot if the size isn’t correct.


One of the top challenges on how to wear men’s boots is width. Often we find boots that are too tight and compressing ultimately cause damage to our feet. You may have tried on a pair of boots with the wrong width and thought that they will stretch. This is a myth that often has people walking around in the wrong shoe size. Not all boots stretch—so when trying on, count on the fit and not the stretch. If the fit fails, dust your boots off and try again.

Style Tip: Need to find your foot width? Measure your feet at home using a piece of paper, ruler, tape and a pencil. Knowing your foot measurements will have you well on your way to finding the proper boot fit. 


Just as boots come in different styles, they also come in varying heel heights. As with any shoe, you want to make sure that the heel height is comfortable for you. Despite how comfy the body of the boot may be, if the heel is uncomfortable, move on to the next. Boot break ups are hard, but your feet will thank you later.


The good ole plantar fascia—also known as the arch of the foot—is a vital component to the comfortability of your boots. The arch is the thick tissue on the bottom of the foot that connects the heel to the toes. If that connection hurts, your whole foot can become inflamed. If the arch of the boot makes the arch in your foot uncomfortable, give those boots a hard pass.

Flex Point

When it comes to how to wear men’s boots properly, flex point is key. Every facet of footwear has a natural point where the shoe bends, and this is the flex point. Generally, it’s at the widest part of the sole, where the toe portion of the boot begins. If this bend does not complement your foot flex, continue the search to find the right boot for you. 

Toe Box

Now that you found the right fit and flex point, make sure the toe box isn’t too tight. What is a toe box, you ask? It is exactly as it sounds—the section of footwear that surrounds the toes. A tight toe box creates friction that will decrease comfort and functionality. Our feet also swell throughout the day, so having extra space in your toe box is key for longtime wear. 

Types of Men’s Boots and How to Wear Them

Now that you have all of the right fit tools in tow, it’s time to discover the right boot type. Boots are one of the top fall trends for men and there are many great styles to choose from. From ankle to biker, we have rounded up the best boot styles for any season. Get ready for some major boot talk. The how to wear men’s boots conversation is just getting started.  

How to Wear Men’s Hiking Boots

Performance-driven hiking boots are ready for all of your outdoor activities. Remember the origin of the boot that we talked about at the beginning of this post? That is exactly what hiking boots are created to do. They are specifically designed to protect your feet and ankles against the elements. From grassy to rigid mountain trails, they will keep your feet comfortable, dry and supported. Pair these rugged boots with black skinny jeans, a soft T-shirt and a denim jacket for everyday wear. When the mountains are calling, sport them with performance pants, your favorite statement T-shirt and layer on a plaid flannel. 

How to Wear Men’s Ankle Boots

I know. Do we really need to explain what these are? They are literally called ankle boots. For the sake of the blog, let’s do it. Ankle boots are versatile boots that rise to the top of your ankle bone. You have to admit that the explanation was fancier than you thought, right? Ankle boots come in many different textiles, textures and finishes. From sporty to sleek, there are numerous styles that work with both casual and dressed-up looks. Wondering how to wear men’s boots in warm weather? Try pairing an ankle boot with a tailored short and a short-sleeve button-up. Keep it relaxed by layering it over a v-neck T-shirt, and you are ready for the dog days of summer.

How to Wear Men’s Chukkas

Chances are, you probably know who Chewbacca is but what about Chukkas? A Chukka (pronounced chuck-uh) boot is an ankle boot that is made of suede or leather uppers. Typically  finished with a rubber sole and laced with two or three pairs of eyelets, Chukkas are built to last. Originally made for British soldiers in the Western Desert Campaign of World War II, Chukkas are spotted everywhere. From streets to runways, Chukka boots are a style staple in men’s fashion. Wear them with a cuffed jean, vintage T-shirt and a sporty blazer for a date or dinner with friends. 

 How to Wear Men’s Chelsea Boots

No guide to wearing boots would be complete without covering how to wear men’s Chelsea boots. This ever-so-stylish slip-on style is characterized by 2 things—ankle height and an upper of two joined pieces. It’s a party in the front and back with a seam in the middle. We also can’t forget the tapered toes. This boot is a classic that will always be on-trend. Pair the Chelsea boots with an effortless jogger and a long-sleeved crew neck T-shirt. Add a tailored vest for a look that is equal parts comfortable and fashionable.

How to Wear Men’s Combat Boots

Combat boots were originally created for military use and have also become a style staple for both casual and elevated occasions. Constructed with ankle stability and foot protection for any environment, designers continue to create their interpretations of how to wear men’s combat boots. With their lace-up design and tapered ankle, combat boots take how to wear men’s boots to new heights. Tuck in a dark skinny jean to your black combat boots. Add a black pullover sweater for a monochromatic look that is perfect for all of your weekend get-togethers.     

How to Wear Men’s Biker Boots

Make sure you have your helmet on for this next boot trend. Actually, don’t. You can wear men’s biker boots without ever getting on a motorcycle. These boots have a low heel, buckle detail and add just the right amount of edge to any outfit. Don them with a slim grey jean, simple white T-shirt and a crisp leather jacket. Want something more laid-back? Swap out the leather jacket for a camel hoodie, and you are all set.

How Should I Style Men’s Boots? 

There have already been some style tips and tricks on how to wear men’s boots, and get ready for more. We have some additional advice, but remember—there is no correct way to wear them. Style is a personal expression that is ultimately your choice. Wear what you feel best in and you can’t go wrong. 

What to Wear with Black Boots

No matter the style, black boots are a neutral staple. A black boot can be paired with any pant, jean or jogger in any wash or color. Once you have picked your bottoms, add a sharp button-up to elevate the look or keep it relaxed with a graphic T-shirt and on-trend cardigan. When it comes to what to wear with black boots, nothing is off limits. 

Style Tip: Rock socks that pop. Adding a vibrant, textured or patterned sock to a black boot can take wearing mens boots to the next level. Roll up your pants and let the socks peek out over your black boots to add interest and experiment with your style.

What to Wear with Brown Boots

Brown boots are another staple that expand any closet they are in. From tan to cognac, brown boots are versatile and pair well with most of the pieces in your wardrobe. Are you ready to give them a try? Wear a printed shirt like a microfloral with a neutral-colored pant. Bring in the brown boots and layer an on-trend shacket to complete the vibe. Refine your look by tucking in the shirt and adding a belt. Add the same brown boots to a pair of distressed jeans. Roll up the cuff to the top of the boot and add a crew neck sweatshirt for another fresh casual take.

How to Wear Boots with Jeans

You can’t talk about how to wear men’s boots without talking about jeans. They complement each other in the best ways and are a combination that will stand the test of time. From skinny to relaxed, your favorite jeans and boots are a dynamic duo. The key to a successful jean-boot look is balance. If the jeans are a relaxed fit, find an oversized shirt to complete the slouchy silhouette. With a skinny or slim option, find a T-shirt that you can tuck or is fitted to the body. Going for a layered jean look? Leave the top layer open and front tuck the base shirt to refine the overall outfit. Don’t be afraid to experiment with silhouette and style when assembling your boot and denim looks.    

Is it time to step into new boots? Take your style quiz, schedule a Fix and ask your stylist for boots to meet your everyday needs. You’re never required to schedule more than one Fix at a time and shipping and returns are always free.

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