Definitive Boot Buying & Style Guide For Men

Boot Buying Guide

Here is my definitive boot buying and style guide.

Your initial question may be, “Why exactly do I need a pair of boots?”

Please allow me to respond to that query with a different one.

Did you know that one of the first three things a lady sees about you is your shoes?

Whether you like it or not, a lot more people notice your feet than you might believe. Giving the ladies something attractive to look at is so crucial.

Boots are a timeless footwear option that are both stylish and practical, in contrast to sneakers, which are continuously changing in terms of styles and trends.

They are the good item for shielding your feet from the weather and keeping their aesthetic appeal at the same time.

But first, let’s talk about some of the most typical boot mistakes that men make before we talk about which boots are best for you.

Most Common Error

The most frequent and harmful mistake I observe men making when selecting a pair of boots is skimping on the materials.

Any boots under $200 are going to be poorly built and ultimately not worth the money, based on my experience.

They might work for a while, but I can assure you that they were constructed using inferior materials and won’t last more than a year or two at most.

What to Avoid?

Avoid synthetic materials and leather blends that contain plastic and other chemicals and choose leather or suede since these materials will last for a long time.

Avoid shoe companies that don’t specify the material they use, and watch out for those that claim to be genuine leather when they aren’t.

Cheaper synthetic leathers will develop wrinkles, peel, and discolor with time, and the level of maintenance necessary to keep them looking good is truly not worth it.

What is Good?

However, genuine leather won’t look or peel; instead, it will develop a patina on its own surface over time, improving the way it looks.

You have two alternatives when it comes to the soles of your boots: glued or stitched.

The more expensive option is stitched soles since they can be repaired after years of usage. While glued soles are less expensive, they cannot be repaired if they are seriously damaged.

You should consider your boots as an investment that will last you for many years because quality comes at a cost.

I usually recommend considering your budget to see how affordable a new pair of good-quality boots would be.

Why not spend $400 on a pair of boots that will last you five or more years instead of spending $200 a year on a new pair of lower-quality boots? And will ultimately look much better.

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What About Maintenance?

Why do we go to such lengths to protect our boots? The reason is ultimately that they protect us.

Fortunately, maintaining a high-quality pair of boots is not too difficult and will pay off in the long run.

Suede is one of my favorite materials for boots. Real suede will conform to the curve of your foot, making it stylish, versatile, and incredibly comfortable.

But because suede does have a fuzzy texture, Scotchgard waterproofing should be applied at least once a year.

Weatherproofing your boots is absolutely necessary if you reside in a region where it frequently rains and snows.

A rubber sole for your boot is a must if you reside somewhere with a climate that is primarily wetter.

A rubber sole is a more resilient and long-lasting option than a leather sole. It is salt and snow resistant in addition to being waterproof. Furthermore, it has an excellent grip.

If you live somewhere that receives a lot of snow, my recommendation is to choose lugged soles. If you live in a particularly rainy area, choose dainite soles instead.

Before picking on a sole for your boots, take the time to consider what they will be used for.

Which Boot Type?

Which style of boots should you invest in?

Given the wide variety of styles available, this question may seem frightening.

Let’s start off with a staple of menswear.

Leather Lace-up Boot

Actually, there are three kinds of lace-up boots to select from.

The dress boot, the fashion boot, and the casual work boot.

The best course of action, in my opinion, is to pick a boot that complements the outfit you’re wearing because each of these has a certain purpose.

The casual work boot is appropriate for less casual settings, as the name implies. This is also the most common option and the one I recommend.

The fashion boot is more of a statement piece that most males should generally avoid unless they truly know what they’re doing, whereas the dress boot is formal wear.

The casual lace-up work boot is unquestionably the most versatile option of the bunch. It has a sleek yet sexy style and a rubber sole that will go with your heavier early spring outfit as well as your more layered fall and winter appearances.

Before experimenting with other colors like black, light brown, walnut, gray, burgundy, and so on, you should choose a dark brown if this is your first time purchasing a pair.

Additionally, stay away from blues and greens because there are very few combinations that can be made with them.

When it comes to pairing, your casual work boots will go with just about anything in your closet, including your jeans, chinos, button-down shirts, and sweaters.

However, the lace-up dress boot excels if you’re looking for a more formal boot in this situation. You may dress up all kinds of outfits with these boots, including suits, wool pants, and sports coats.

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Don’t be scared to cuff the bottom of your pants if they are a bit too long when worn with boots; this definitely adds your outfit a stylish finishing touch.

Chukka Boot

Next, we have a boot that truly ranks as my top pick. It’s the chukka boot.

Chukkas are incredibly lightweight and versatile ankle boots, and one of its best features is that they work for all body types.

They’re a fantastic alternative for spring and fall, and if selected in the proper shade and fabric, they may even be worn in the summer and winter.

Chukkas are the ideal transitional boot between lace-up boots and sneakers. They have the effortless ability to really enhance all different kinds of outfits, which is one of my favorite things about them.

Even though there are dressier options available, a casual pair would likely work for many of your more formal outfits, including business casual and your jeans and sweater combinations.

Chukkas come in leather and suede as far as materials go. My personal favorite material is suede since it adds a second layer of texture to your outfits, which look especially great in the cooler months.

If this is your first pair, I recommend choosing a medium brown because it is undeniably the most versatile color.

If you already have a pair of medium brown shoes, however, you should add black to your rotation.

I would advise staying away from blue, green, and walnut because they will be more challenging to work into your current wardrobe.

Your pants’ hem should have little to no break when it comes to fit. Just remember to cut the bottom of the pants if it’s a little longer. It adds a wonderful bit of style.

The major drawback of chukkas is that, if you choose suede, rain and snow will be really bad for the material. Even if you Scotchgard them. Go with leather if that is the weather where you live.

Additionally, you cannot wear casual chukkas with formal attire, such as suits, as this just looks completely out of place. If this is the situation and you are wearing more formal outfits, such as suiting, dress pants, or sports coats, I would suggest wearing a dressy formal chukka.

Chelsea Boot

The Chelsea boot is unquestionably the most dressy of the three boots.

They feature a very compact and sleek style that makes it simple to give your outfit an extra touch of polish. The Chelsea is offered in leather and suede, just like the chukka.

If you’re going for a more casual look, I usually advise getting a suede Chelsea, whereas a leather Chelsea looks best with more dressy attire.

In terms of color, a Chelsea in both dark brown and black will cover most outfit combinations. Tan or a lighter shade of brown are colors I’d steer clear of because they’re difficult to pair with outfit.

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One thing to keep in mind is that while the Chelsea is a sleeker boot, it must be paired with a similarly sleek outfit.

As a result, the leg of the pants must be tapered from the knee to the ankle. Chelsea boots do not, however, work for all body shapes because of this.

Choose a different boot style, such as a lace-up boot or chukka, if you have extra weight in your upper body. The sleeker Chelsea boot’s combination with tapered pants will throw your upper and lower body out of proportion and make you appear extremely top heavy.

Outfit Ideas

Always and without exception, a man who is dressed in well-cut casual attire will look more put together than a man who is dressed in a sloppy suit. You should keep that in mind as you choose your outfits to go with your new boots.

The best advice I can give you is to experiment with the clothes you already own.

But if you need some ideas, here are three outfits that show you just how to wear various styles of boots.

The first outfit is a casual one that includes a pair of lace-up brown leather boots.

You can choose to wear a camel crew neck sweater over a button-up shirt, along with dark wash denim jeans and a stylish trucker jacket as outerwear. Fall is clearly in the air with this outfit.

The next outfit is also casual but stylish and has a fall-inspired feel. Olive green chinos and a dark blue crewneck sweater are paired here with gray suede Chukka boots. One of my preferred color combinations for fall is blue and green.

This color of chukka is not required for you to wear. You could also choose a traditional medium to dark brown.

A sleek pair of leather Chelsea boots is included in the last outfit. Put them on with a pair of tapered black denim jeans and a button-up shirt layered beneath a Barbour quilted jacket.

Barbour jackets are warm and lightweight, but you could easily replace this one with a sports coat or blazer to give the outfit a more formal look.

Boot Style Guide


  • Christopher

    Christopher has 9+ years of experience as a creative fashion designer who stays current with the latest trends.

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