10 Best Types of Boots for Men (and My Top 3 Picks)

If you’re building up your boot collection or buying your first pair of boots, you might be wondering which type of boots to buy.

There are so many different types of boots, from chukkas to Chelseas, and it can be confusing trying to figure out which ones are right for you.

Obviously, it depends on your lifestyle. The business professional is going to have slightly different requirements than the college student.

But I think that there are three types of boots that pretty much any type of guy could get a lot of wear out of. If I were starting from scratch, these are the boots I would buy first (in no particular order).

Note, the examples below are all from Thursday Boot Co., my #1 recommendation for boots under $200.

I’ve been wearing this brand for years, and the boots have aged well. You can check them out right here.

#1: The Dress Work Boot

The dressy work boot is a great first boot for anyone. I say “dress” work boot because, while this type of boot is styled after a work boot, it’s not necessarily meant to be used for manual labor.

Just like many types of boots (and other fashion-related products, such as jeans), the dress work boot is a descendent of utility – in this case, intensive manual labor.

While these boots could take a beating, I think they’re best used to create stylish outfits with rugged, masculine vibes.

Simply put, these boots are handsome. Personally, I think this dark brown color is a great first choicer most guys, although black is a good option if you wear a lot of black, white and grey.

Dress work boots look awesome with jeans (pretty much any wash), chinos and even trousers if done correctly.

But I’d probably avoid this type of boot in business casual settings, and they should definitely be avoided during formal settings.

The only other time you wouldn’t want to wear these is with shorts, but that goes for pretty much all boots.

Unless, of course, you’re a carefree man-child who has completely given up on his appearance!

#2: The Chukka Boot

The chukka boot is basically just an ankle-high boot. It’s often used to describe desert boots, which are a specific type of chukka.

Desert boots are ankle boots with crepe soles and soft suede uppers. They were worn by British soldiers in North Africa during WWII.

Desert boots, like the J. Crew Macalister, are usually pretty casual, while chukka boots can be pretty dressy.

The big difference is the sole and the upper. For example, this pair of Thursday Boot Co. chukka boots has a structured upper, rather than the soft upper of the Macalisters.

If you got this pair in black leather, it would be pretty dressy, compared to a grey suede desert boot.

I think a standard chukka boot is a great choice for anyone – from college students to business casual professionals. If it’s your first boot, I would go with dark brown.

If you’re expanding your collection, consider suede instead of leather. But make sure you find water-resistant suede if you live somewhere that rains a lot.

Regardless of whether you go with suede or leather, chukkas look great with jeans and chinos. They’re similar to dress work boots but a step up in terms of formality (which makes them more appropriate for office settings).

#3: The Chelsea Boot

The Chelsea boot is cool because it can worn in place of work boots or chukka boots, but it can also be dressed up a bit more, especially if you go with dark brown or black leather.

In fact, it’s not uncommon to see men wearing Chelsea boots with suits these days.

So, if you’re a working professional in a somewhat formal office setting, or if you live in a fashionable city like New York, you might consider buying a pair of Chelsea boots first.

On the formality spectrum, they’re closer to chukka boots than work boots, but you can still dress them down.

Of course, it depends on the material and color. For example, tan suede Chelsea boots with lighter wash jeans is a classic combination.

I really like the light brown suede Chelsea, so if you’re looking to add some variety to your shoe collection, this would be a solid choice.

Either way, the Chelsea boot is a classic, versatile boot that’s easier to pull off than most men think.

And I mean that literally, by the way. Since it has no laces, this boot is very easy to put on and take off, which also makes it great for air travel.

Building a Well-Rounded Boot Collection

Since these three boots can often be used interchangeably, I recommend varying up the colors and materials. For example, my collection consists of:

1. Dark brown leather work boots
2. Dark blue suede chukkas
3. Light brown suede Chelsea boots

Here are all three, side by side:

But you could also go with something like:

1. Black leather work boots
2. Light brown suede chukkas
3. Dark brown Chelsea boots

This way, you have a variety of styles, colors and materials to choose from.

Once you figure out which boots you tend to wear most often, you can always add another option to the mix. For example, I love having the grey suede desert boot as a more casual alternative to the dark blue chukka.

Your Turn

What kind of boots do you wear? Do you prefer chukkas or Chelseas? Let me know in the comments section!