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Best Men’s Chukka Boots of 2019: Complete Reviews with Comparisons

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Chukka boots are a staple for any fashion-conscious man, and they have been for decades. The origin of these boots is a bit cloudy, but it was a popular style in the UK around the 1920s.

In fact, they were so well-known that the Duke of Windsor, who was previously King Edward VIII before he abdicated the British throne for love, was commonly seen in them.

Now, don’t get us wrong. You don’t have to be a king or even a duke to look great in a pair of chukka boots.


Comparison Chart

Skechers Men’s Segment Melego Leather Chukka Boot
Skechers Men’s Segment Melego Leather Chukka Boot
Dr. Martens Bonny Boot, Black, 9 Medium UK
Dr. Martens Bonny Boot, Black, 9 Medium UK
Nunn Bush Men’s Lancaster Chukka Boot,
Nunn Bush Men's Lancaster Chukka Boot
Timberland Men’s EK Brook Park Chukka Boot
Timberland Men’s EK Brook Park Chukka Boot
Eastland Men’s Seneca, Bomber Brown
Eastland Men’s Seneca, Bomber Brown

Best Men’s Chukka Boots Reviews

1. Skechers Men’s Segment Melego Chukka Boots

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Skechers Men’s Segment Melego Chukka BootsThe Skechers Segment Melego Chukka Boots is a great middle-of-the-road option for those who like the look of chukka boots yet looking for something a bit more rugged. They are waterproof, made of 100% leather, and they almost look like a hybrid of traditional Oxford shoes and chukka boots.

Features

One of the options that we have chosen to review is this pair of chukka boots from Skechers. Though not traditional chukka boots, this pair certainly has a place on the market and is a good option for people who like the look of chukka boots but need a bit more.

These boots are waterproof, and they have an outsole that has a great deal of traction. The tongue and collar are padded, and thanks to the relaxed fit, the shoes are comfortable and roomy. To add to these already great features, these boots are also designed to have a memory foam comfort insole.

PROS
  • 100 percent waterproof
  • Memory foam gel insole
  • Very comfortable to wear
  • True to size
CONS
  • Only two color options: brown and black
  • A bit more expensive than other chukka boots on the list
  • Some say that the shoe squeaks a lot when walking

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2. Dr. Martens Men’s Bonny Chukka Boots

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Dr. Martens Men’s Bonny Chukka BootsAnother option for those looking for the best men’s chukka boots is the Dr. Martens Men’s Bonny Chukka Boot. As you might expect from Dr. Martens, these boots are well-designed and made from high-quality materials. Of course, for these benefits, you can assume the price to be a bit higher and with a cost that is similar to other Dr. Martens footwear.

This pair is crafted from nylon, so it is guaranteed to be durable and long lasting. It is available in a full range of sizes in the colors black and olive. You probably know that Dr. Martens’ shoes are pretty tough, but are they the best men’s chukka boots of the year? Let’s find out!

Features

These boots are really durable, and as with most Dr. Martens creations, they are definitely going to last for many years. When you put them on, you can feel the quality, and you might notice that it feels as if you are walking on air. That is because you are, thanks to the air-cushioned chambers throughout the sole.

These boots are designed to be slightly wider than other shoes, so if you have a narrow foot, you might not want to go with this option. However, for those with a typically average foot width, you will probably like the extra room that these boots offer.

There are five eyelets on these boots, which is a bit more than the typical two or three eyelets on a traditional chukka. Then again, Dr. Martens certainly isn’t known for toeing the line with any design.

PROS
  • Fits as expected
  • Has a roomy feel
  • Comfortable, air-cushioned sole
  • Lasts for years
CONS
  • A bit on the pricy side compared to other chukka boots
  • Not a traditional chukka boot style
  • People with wide or narrow feet might have a problem with comfort

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3. Men’s Nunn Bush Lancaster Classic Chukka Boots

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Men’s Nunn Bush Lancaster Classic Chukka BootsThe Nunn Bush Lancaster Chukka Boots comes in a classic style, so it is an excellent choice for men who are looking for a traditional pair of chukka boots. You can easily pair these shoes with chinos, jeans, or khakis for a relaxed, casual look.

These boots are available in leather or suede, which gives you even more choice when deciding if these boots are the right pair to add to your wardrobe. Let’s look at its features below.

Features

Comfort is key when it comes to choosing a new pair of boots, and the Nunn Bush Lancaster Chukka Boots are definitely one of the most comfortable ones we have reviewed. The plain toe design lends to the classic look of these boots.

The insole is made of memory foam, so it definitely feels like every step you take is cushioned. As a matter of fact, the design of these shoes takes it a step further, and over time, the insole creates a custom fit for your foot.

There are three eyelets on these shoes, which allow you to get a custom fit, and you can choose to get wide boots if you need them. You can choose from brown, black, or camel, and the sizes range from men’s 7 to 13.

PROS
  • Has a classic, traditional look
  • Memory foam insole cradles and shapes to the feet
  • Available in wide or medium width
CONS
  • Some report a chemical smell coming from the boots
  • Stiff construction that must be broken in
  • The medium width version might be a bit smaller than other medium-width boots

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4. Timberland Men’s EK Brook Park Chukka Boots

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Timberland Men’s EK Brook Park Chukka BootsIf you’ve ever heard of any shoe brand known for high-quality shoes and boots, it is likely Timberland. The brand’s EK Brook Park Chukka Boots is very well-loved, which ensures that this pair of boots is one that you should take a close look at if you are in the market for chukkas.

Features

The EK Brook Park Chukka Boots from Timberland is a traditional style chukka. These ankle boots feature two eyelets, and they have a small, 0.75-inch heel. Made using leather, these boots look sleek, have contrast stitching, and a heel that is also accented with leather.

The laces are made of cotton, and the linings are created using 50% PET, which is made with recycled plastic bottles. You will also find that these boots are remarkably comfortable to wear, thanks to anti-fatigue technology that makes your feet feel great.

As for the sizing, keep in mind that this pair tends to run a half size larger than other chukka boots.

PROS
  • Comfortable from the moment you put them on
  • Made of high-quality materials like leather
  • Traditional chukka boot design
CONS
  • Sizes run a bit larger than other boots
  • Laces don’t last too long
  • Higher price than other chukka boots

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5. Eastland Men’s Seneca Chukka Boot

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Eastland Men’s Seneca Chukka BootWe close our reviews with a look at the Seneca Chukka Boots from Eastland. You are probably familiar with the brand, especially since it has been around ever since 1955. Also, you will find that with competitors like Timberland and Dr. Martens, Eastland is in good company.

The price is right for these boots, most of which start at under $50. They come in both leather and suede materials. Other features that make it stand out from the crown are listed below.

Features

Though there is no doubt that the Eastland Men’s Seneca Chukka Boots is a great shoe, if you are looking for a traditional chukka boot, this might not meet your needs. Where chukka boots should have two to three eyelets, for instance, this boot has five! So, you definitely will need to get longer laces and keep the design change in mind when planning your outfits.

This pair is available in a huge range of colors, which is something that other boots on this list can’t match. You can tell that the shoes are constructed with great detail in mind, as well as designed with comfort, thanks to the comfort insole that forms around the foot when you walk.

PROS
  • Affordable cost compared to other chukka boots
  • Soles form around the foot when walking
  • A wide range of colors and sizes available
CONS
  • Not a traditional design for a chukka boot
  • Soles do not have a lot of traction
  • The material is thin and not very warm in the cold weather

CHECK LATEST PRICE ON AMAZON.COM


FINAL VERDICT

We took a good, hard look at these men’s chukka boots, and we were able to make a solid decision about which one is the best of the best. Before revealing that information, though, we want to say that all of these boots are great options, so you might have to look closely at the details, the pros, and the cons to determine if that particular pair is the one that you are looking for.In the end, we chose the Timberland EK Brook Park Chukka Boot as the best of the year, and there were a few reasons why it stood above the rest. First, it is a pair of classic and traditional chukka boots. Other boots that we looked at did not follow the style that is mostly associated with the chukka.Another reason this boot stood out from the rest is that they are immediately comfortable from the moment you put them on. If there is one thing that would stop someone from buying these shoes, it might be the price.If you are looking for something good but a bit more affordable, you should consider the Nunn Bush Lancaster Chukka boots. These, too, are traditional in their design, but they are not as expensive as the other boots on this.

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