11 Types of Men’s Boots Styles and When to Wear Them

Best Men's Boot Styles Featured

Whether it’s fall, you’re going hiking, or just want a better alternative to sneakers, it’s time to find the best men’s boots! I used to be a sneakers-only guy, but one day I decided to try on a pair of boots at a local Clarks store and fell in love with how much more like an adult they made me look. Since then, I eagerly where them whenever I get the chance.

But not all men’s boots styles are right for everyone. Even for myself, I mainly stick to three styles because they fit the best with my personal sense of style. So going into this list, don’t feel like you need to have all of these boots styles – but I do encourage you to at least try them out at a local shoes retailer to see how they look on you. You might be surprised!

1. Chelsea Boots

Chelsea boots are laceless boots with elastic side ankles that make them easy to slip on and off as necessary. Leather chelsea boots can be worn in smart casual and business casual outfits, and polished black chelsea boots may even be able to fit into a semi-formal outfit. However, unless you have the confidence to pull them off, you may want to reserve chelsea boots for casual outings only.

2. Desert Boots

Desert boots, also known as chukka boots, are a three-season men’s boots style best worn in the spring, summer, and fall. They only cover the ankles and don’t have many eyelets, so they’re extremely well-ventilated – perfect for hot and muggy weather, terrible for biting cold winters. Leather desert boots are stylish for all ages, and lean heavily toward the casual side of the formality spectrum. Wear them with jeans, chinos, or non-athletic shorts for best results.

3. Combat Boots

Combat boots, also called military boots, are robust and chunky with thick soles and lots of eyelets for tight lacing up and down. They’re trendy and casual – you don’t want to wear these with anything more proper than a pair of well-fitted jeans or leather pants. Best worn in the fall and winter for warmth and insulation.

4. Duck Boots

Duck boots, a style made popular by L.L. Bean’s Bean boots, are iconic winter-style boots with a rubber lower section and a leather upper section. While both rubber and leather are waterproof in practice, duck boots are more robust in wet weather because rubber doesn’t succumb to excess water like leather does. At the same time, the leather upper is more comfortable to wear than a full rubber boot. Duck boots are trendy, casual, and perfectly stylish for frigid winter climates.

5. Moc Toe Boots

Moc toe boots have a seam that runs around the front-top of the shoe, and they’re named because the style was inspired by the design of the moccasins worn by Native Americans. Moc toe boots are surprisingly comfortable, and remain one of the most casual boots styles available to men. They’re trendy, can be worn with just about anything, in any season, and are unique in that they’re one of the only boots styles that come with white sole options.

6. Rain Boots

Rain boots are purely worn for practical reasons: either it’s raining so much that even duck boots won’t save you, or you’re planning to wade through a marsh and don’t want to develop trench foot. It’s hard to look good in rain boots, but if you want to try your best, stick to ones that are as plainly designed as possible. Anything that doesn’t draw attention to itself.

7. Work Boots

Work boots were originally designed for safety and longevity in rough working environments (think construction), but they don’t have to be worn only for work. In fact, these are one of the most stylish boots options available to men. Any man can look good wearing a pair of trendy work boots paired with well-fitted jeans or chinos and a slim-fit gingham shirt. Of all the boots in my collection, my work boots get the most compliments.

8. Ankle Boots

Ankle boots are similar to Chelsea boots, but don’t feature the elastic sides. If you need more room to slip them on, opt for ankle boots instead that feature a zippered side. These won’t stretch out as easily with repeated wear, but they’re not too comfortable if you have more muscular ankles. A sleek black or dark brown works in many business casual settings. But, they work best with khakis, chinos, and jeans for casual, everyday wear.

9. Dress Boots

Dress boots are the best men’s boots style for more formal occasions. While you can get dress boots in chukka, Chelsea, and ankle varieties, they all share one thing in common – they look like the boot version of a typical dress shoe. They’re often higher quality and made to look incredible with dress slacks and chinos. While you can pair them with jeans, they’re kind of overkill. I’d recommend leaving this for special occasions only.

10. Cowboy Boots

Cowboy boots are both casual and more formal, especially when paired with dark fitted jeans. They have slightly higher heels and are made for riding horses. Of course, they’re also comfy for daily wear, though the soles do tend to take a while to break in. They come in both ankle and mid-calf varieties along with being either plain or more embellished. Adding a cowboy hat to the mix is completely optional.

11. Hiking Boots

If you’re planning on hitting the trails, you need a great pair of hiking boots. Think of them as a mix of a work boot and sneaker all in one. These are more rugged and often have better tread and soles for long days of walking on uneven terrain. They’re as casual as it gets, so don’t pair these with your slacks for a day at the office. Depending on where you’re hiking, look for features like waterproof, insulated, and ventilated. If you’re a die-hard sneaker fan, try these sneakers made for cold, winter weather.

Frequently Asked Questions

Why are boots harder to break in?

The hardest part of transitioning to boots for me was how much longer it takes to break them in. But, trust me, when you do break them in, you’ll love how much more durable they are. They often have tougher soles, which gives you more support, but aren’t as forgiving at first.

Can I wear boots to the office?

Some offices with a casual or business casual policy do allow certain types of boots. Usually, you should avoid anything that has more of a sneaker quality. If you’re not sure, just ask HR about the dress code.

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