You can tell a lot about a man from his choice in footwear, and when it comes to choosing shoes you will be hard-pressed to do much better than a sturdy pair of leather boots.

Boots are the most perfect example of men’s style fitting the three f’s. Leather boots are the most functional things you could wear on your feet (again, this excludes sport-specific technical items), are always purchased to fit extremely well, and they will look better and more fashionable the longer they’re worn.

But with so many options to choose from, it’s easy to be led astray. Luckily for you it only take a little bit of knowledge to ensure you make the proper choice and buy boots you will love for decades.

How to Buy Great Boots

The most stylish boots you can ever own are going to be the boots that will last you the rest of your life. You’re looking for stiff, thick, leather, welted, and hand-made. Sure, they’re extremely expensive up front, but after 20 years of wear they will be, comparatively, the cheapest article of clothing you own.

Not all leather is equal

Unless you’re buying something temporary, or trendy, the only material you should ever consider when buying boots is leather. Nothing else is going to last for life. When it comes to leather, there’s a little bit of information you need to know.

Good boots get better with wear.

Good boots get better with wear.

First, and most importantly, you are looking for full-grain leather. Bonded leather is cheaper, but for good reason. Think of bonded leather like particle board, or plywood, while full grain leather is a plank of maple. Bonded leather will start to fall apart, look terrible, and need to be replaced in short order. True leather will only look better as time goes on.

The animal the leather comes from matters as well. Leather from different animals has different feels, looks, and durabilities. For example, deerskin is extremely soft. While ideal for leather gloves, it’s a terrible choice for boots.

Excluding cowboy boots, the only type of boot leather you really want to pay any attention to is horsehide and cowhide. They are the thickest, and stiffest you will get, meaning they are going to last the longest.

Don’t sell your sole for style

If you’re buying boots to last you the rest of your life you need to pick up boots with replaceable soles. This is known as “welted”, referring to the strip of leather (known as a welt) which connects the out-sole (the part that touches the ground) with the upper (the part on your foot).

Don’t be fooled by stitching around the perimeter of your shoe. Many cheap shoes will have ornamental stitching around the sides (it’s even part of the design of rubber soles on Converse) to make their shoes look more ‘classic’ or ‘quality’. Be sure the stitching is functional, and the soles can be replaced when worn-out.

How to know if your boot fits

Finally, we get to the most important part of any piece of fashion: it needs to fit. If you’re going to buy something once, and wear it for decades to come, you need to get the fit correct the first time. Clothing only looks and feels great if it fits properly. When it comes to boots this means length, width, and insole.

Viberg tan horsehide. Top of my list.

Viberg tan horsehide. Top of my list.

Most high-quality boot makers don’t stock set sizes of boots. They are all made to order. This doesn’t mean they are bespoke (made specifically to your exact measurements). Shoes are made around a ‘last’, basically a wooden foot. Most boot makers will have lasts in a variety of lengths and widths, and will make your boots to the last most closely matching the dimensions of your foot.

True bespoke boots are made around lasts carved as an exact replica of your two feet. If you have the money to do such things, good on you. But for us mere mortals, getting boots made to your size is as close as we will come.

I will warn you: properly fitting, new, leather boots are not comfortable. Well fitting BIFL leather boots are difficult to get on, take off, and hurt your feet until they are broken in. This is a recurring theme you will find in men’s style: almost all the best things you can buy, suck until you put in the time.

Now don’t get me wrong, I’m not trying to say you should only own a great pair of boots. You can own any number of shoes you like. You could write a book on what shoes to where to what, but it doesn’t interest me enough to want to think about that junk. Just get a great pair of boots, and wear them often.

Moving up from your feet, the third article in this series deals with pants. More importantly, it’s a guide to jeans.