Best Mens Boots [ULTIMATE LIST]

Boots are a staple shoe in menswear. In my case, I own several pairs that I enjoy rotating depending on what I’m doing and where I’m going. Oh, and the weather is a big deciding factor, too. I wouldn’t sport my tan suede chukka boots when we just had a nasty Canadian snowstorm, for example.

With that being said, every man needs a pair of boots in his wardrobe. They’re fashionable, sophisticated, and versatile. You’ll get a boost in confidence, looks from the ladies, and will have no shortage of outfit ideas.

That’s why I’ve curated this hand-picked list of the best boots for men. There’s a variety of categories and styles to suit your individual needs. Enjoy

Best Mens Dress Boots

The dress boot originated in the Victorian Era, where it was normally worn as eveningwear. Men rarely would wear shoes, as boots and court slippers were the footwear of choice.

While tall riding boots composed of patent leather or calfskin were the norm, shorter dress boots were kept for very formal occasions. Just like today, they were characterized by having the appearance of a standard dress shoe, expect that it extended past the ankle.

Are Dress Boots Formal?

Today, dress boots can be worn both casually and formally. It depends on the individual style of the boot and how it’s worn. For example, a simple dress boot with little to no broguing would be formal. A dress boot with a wingtip design and medallion toe would be considered casual.

Are Dress Boots Comfortable?

I’ve owned multiple pairs of dress boots and can say that they are a very comfortable footwear. Comfort also depends on the brand you buy from, of course. Leather like calfskin molds to your feet, versus synthetic leather that tends to be more stiff. I also recommend looking for dress boots with leather lining to increase breathability and as special insole, such as memory foam.

Can You Wear Dress Boots With A Suit?

It’s not traditional, but it works. As I previously mentioned, the simpler the dress boot, the more formal it is. If you’re going to sport a pair with a nicely tailored suit, ensure that your boots are as simple as possible. After all, they are supposed to resemble a dress shoe, hence the name, and trousers should cover the upper portion.

Can You Wear Dress Boots In The Summer?

Unless you enjoy having your feet swim in a pool of sweat, it’s not recommended to wear dress boots in the summer. You want your feet and ankles to breathe during the warm months, so stick to loafers, sneakers, and similar casual shoes.

Thursday Boot Company Captain Men’s 6″ Lace-up Boot

The Captain is a minimalist dress boot with a stunning cap toe. It features the famous Goodyear welt construction, meaning that these boots can last a lifetime and are extremely robust.

And it doesn’t just look good, it feels good, too. The lining is all leather, keeping your feet breathing and comfortable all day. High quality leather ages with time and molds perfectly to each foot. Thursday Boot Company also added cork and poron footbeds to make each step bouncy and light.

The stacked heel and studded outsole add height to your stance and provide extra grip for damp weather.

Steve Madden Men’s Jefries Combat Boot

The Steve Madden Jefries boot boasts a burnished look that adds an aged and sophisticated element to a classic silhouette. The cap toe and stitching detail adds extra style to these versatile boots. Pair them with jeans and a knitted sweater for an easy fall look, or throw wool trousers over them when you head to the office.

Jefries are composed of leather, and gradually shape to your feet the more often you wear them. The outsole is composed of a synthetic material which ensures that you can sport them more often and that they last longer.

Florsheim Men’s Foundry Cap Toe Dress Casual Boot Oxford

Florsheimis one of the most popular men’s dress shoe brands, but they also sell incredibly fashionable boots. The Foundry cap toe dress boot has a classic appearance you can pair with any pants and shirt.

It’s made out of high-quality Chicago leather that’s durable and long-lasting. The pull tab makes these slide on like butter, and soft lining prevents your feet from itching or scratching.

Best Mens Chelsea Boots

The chelsea boot is a unique thing in menswear. It sprouted many decades ago, and came back to life in recent years. It’s characterized by its close fit, elastic sides, ankle height, and slim silhouette.

J. Sparks-Hall, Queen Victoria’s shoemaker, can be given credit for this wonderful boot. They were a popular riding boot, and Sparks-Hall advertised them commonly as “patent elastic ankle boots.”

It wasn’t until the 1950’s and 1960’s that the chelsea boot became popularly worn by men in the UK. Do you know which group gave them a big boost in attention? The Beatles! Look at them here.

Are Chelsea Boots Good For Winter?

Chelsea boots are a fantastic winter boot, but you do have to keep one thing in mind. Chelsea boots often come in beautiful suede leathers that can make anyone drool on sight. However, suede is easily damaged by rain and snow, exactly what you’ll be facing in a winter(especially here in Canada).

That’s why I suggest you get chelsea boots in a regular leather to avoid this issue. You of course will still have to apply a protective spray and avoid water, but it will be much easier to take core of

Are Chelsea Boots Formal?

Chelsea boots were invented for Queen Elizabeth, so it’s fair to claim that they are formal in nature. But, make sure that you wear suit pants that cover the upper portion of the boot so it resembles a dress shoe. That’s the goal with any boot really when you want to make it appear formal and sport it with a suit.

Thursday Boot Company Duke Men’s Chelsea Boot

Thursday Boot Company did more than 20 re-designs to get the shape of the Duke chelsea boot just right. That shows how much effort they put into quality control and creating the perfect footwear for you.

This chelsea boot is handcrafted with high quality leather. The overall design is sleek and simple. You can dress it up or sport it casually. Whatever you feel like it. The elastic sides and large pull tab makes sliding them on easier than stealing candy from a baby.

The lining is made with glove leather, creating a cool and soft touch when you get your feet inside. The cork and poron footbed is so incredibly comfortable that you’ll wonder why you never bought these sooner, as well.

CLARKS Men’s Bushacre Hill Chelsea Boot

When I think of Clarks, I Instantly think of their famous desert boot. However, they also make chelsea boots that will improve the style and confidence of any gentleman. The Bushacre Hill is the perfect example of this.

It is a chelsea boot made out of premium leather and stretch gore side panels. They’re super easy to get in and out of, preventing the common dilemma of spending 10 minutes to get your shoes on and off.

Smooth textile lining keeps you cool and comfortable throughout the day. Your ankles won’t be getting nipped in these suckers. The outsole is also composed of a robust rubber, adding extra grip and longevity.

Blundstone Dress Series Chelsea Boot

The Blundstone chelsea boot instantly stands out with its signature double pull tab. This has to be the easiest boot you can get your feet into. If you’re a gentleman that appreciates convenience, this is the chelsea boot for you.

This boot is composed of 100% leather that boasts a beautiful texture and appearance. People will almost break their necks from checking you out in these.

And they don’t just look great, they feel even better. The removable footbed was created to be anatomically shaped, giving your foot the best possible support. The heel are also features poron shock protection.

Lastly, the outsole is made out of TPU and the midsole is PU. Combined, they create long lasting support that will keep you sporting this boot or many years.

Best Mens Chukka Boots

Chukka boots are ankle high boots with two to three eyelets. You will find them with more, but most stick to the traditional few. They’re available in suede or leather uppers, rubber or leather soles, and also feature open lacing.

The chukka boot is a bit of a wild card, with many stories claiming to be the true origin. What we do know is that British soldiers were posted in India during World War II, and commonly witnessed locals playing polo in a similar boot. These soldiers began wearing them and brought pairs home, sparking brands like Clarks to make similar products.

Nowadays, the chukka boot is a staple in menswear and you’d be nuts to not have a pair. They’re sexy and simple. Throw them on with a suit for that special day, or with just a pair of jeans when grabbing coffee.

Are Chukka Boots Good For Winter?

Chukka boots can be fantastic winter boots for men. I’d suggest that you avoid suede, as I mentioned with the previous boot styles. Suede can get damaged by snow and puddles, and trust me, I know from experience. There’s nothing worse than getting a huge water stain on suede

Are Chukka Boot Formal?

Chukka boots can be pulled off with formal attires very easily. The key is to wear a chukka boot that has two to three eyelets, little visible stitching, and a simple color. Like I was talking about with dress boots, you want a chukka to resemble a dress shoe as much as possible when pant cuffs lays over it.

Cole Haan Men’s Ogden Stitch Chukka II Boot

The Ogden chukka boot features the classic three eyelets, convenient pull tab, and versatile appearance that we all know the chukka to have. High quality leather and suede with rich textures give this boot a high end look that will make you the best dressed man in the room.

The interior is partially lined with leather, creating a comfortable and breathable environment for your foot. Lastly, the textured rubber outsole gives you extra grip for slippery conditions.

Tommy Hilfiger Men’s Gervis Chukka Boot

The Gervis chukka is a casual boot with the timeless Tommy Hilfiger name on the tongue and beneath the brand color pull tab. It’s available in a luxurious olive, brown, grey, and navy suede that’s sure to boost the look of any outfit.

These are a bit more on the casual side because of their bold branding, so try wearing them with jeans or chinos and a sweater. They’re made to feel light, allowing you to sport them all day with ease. An EVA rubber outsole gives every step more traction, as well.

Allen Edmonds Men’s Dundee 2.0 Chukka Boot

Few brands can live up to the name of Allen Edmonds. They are recognized as one of the greatest shoemakers in the world, and the Dundee 2.0 chukka is an example of their craftsmanship.

This boot features a double butyl outsole and an insole composed of poron, creating unmatched comfort and longevity. Allen Edmond s hoes are also recraftable, meaning that you can keep your pair for life.

The raised toe allows for more shine to pop on the walnut leather, and the artisan level layering on the side will catch anyone’s eyes. A 360 degree Goodyear welt construction also turns the Dundee into a tank, adding incredible amounts of durability.

Best Mens Boots Brands

Which brands make the best mens boots? With so many options, it can be a tough decision. These are what I believe, along with user reviews and reports, to be the best five.

  • Allen Edmonds: They have been producing handmade mens dress shoes since 1922, and easily have one of the greatest reputations in the shoemaking community. You are getting extremely high level craftsmanship and detail when you buy boots from them. They also have their “factory seconds” available, which are more affordable footwear that have slight defects — most of which aren’t noticeable. Their recrafting service is extremely convenient, as well.
  • Clarks: I don’t think I know a single man that hasn’t owned a pair of Clarks boots. It’s like a rite of passage in menswear. For the price, style, and quality, you can’t go wrong. I suggest getting their classic desert boot.
  • Red Wing: For over a century, Red Wing has been making functional and stylish mens boots. They’re meant for the hardworking American man that also wants to be confident and look good. They also offer a repair service if you need to restore your boots back to their original appearance, saving you from buying new footwear in the long run.
  • Trickers: It doesn’t get much better than handmade English boots. With premium leathers like kudu and outsole materials like dainite, Trickers makes some of the most stunning and long lasting mens boots available. You’ll find an assortment of styles, including chelsea boots, chukkas, dress boots, and more.
  • Belstaff: For the fashion forward man. Belstaff is a designer footwear brand, using calfskin leather, injected lug soles, and superior detailing that you won’t find any where else. Everyone will drop their jaw when they look at your feet.

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