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Best Looking Men’s Chukka Boots Review

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Looking for a good looking pair of chukka boots? Then you have come to the right place.

Chukka boots are famous for their classic and smart design yet still provide a slightly casual look. They come in various colors and styles, and are perfect for wearing to almost any occasion be it work, vacation or simple everyday wear.

If you are looking to purchase a new pair of chukka boots but not sure where to start, we have found 3 pairs of the best-looking men’s chukka boots on the market right now, which you are sure to love.

Best Looking Chukka Boots Comparison

SOREL Men’s Madson Chukka Waterproof Boot

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Nunn Bush Men’s Galloway

Nunn Bush Men’s Galloway Classic Chukka Boot

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Dr. Martens Men’s Cabrillo Chukka Boot

Dr. Martens Men’s Cabrillo Chukka Boot

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Best Looking Chukka Boots Reviews

SOREL Men’s Madson Chukka Waterproof Boot

Sorel - Men's Madson Chukka WaterproofThe first pair of chukkas on our list is the Men’s Madson Chukka waterproof boots by SOREL. These boots feature a beautiful suede design and come in 8 different color varieties. We take a more detailed look at these stylish boots below.

  • Suede design
  • Strong synthetic sole
  • Waterproof upper
  • Seam-sealed construction
  • Synthetic lining
  • Memory foam footbed
  • Long-lasting wear
  • The sole seems to separate from the bottom of the shoe not too long into ownership

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SOREL is a popular shoe brand who craft shoes for men, women and kids. Their range is varied and offers many shoe styles which are always trending on the market. Their men’s chukka boots are certainly a good option to go for and feature a very nice look.

Timeless look

Are you looking for a pair of boots that really offer that timeless appearance, and will give you an edgy look? Then these boots will suit you well. Thanks to their unique styling they will match most outfits, and will really complement a good pair of denims.

Long-lasting and waterproof

These chukkas have been made to last. With a waterproof upper and seam-sealed waterproof construction, they will be perfect for wearing even in the soggiest of days.

8 colors to choose from

If you purchase a pair of these chukkas and really like them, luckily for you, you have the opportunity to buy them in a few different colors which range from beige, camel brown, crouton, quarry, crouton, elk cordovan, and black. These boot colors all feature a rustic feel.

SOREL Men’s Madson Chukka Boots Price

Nunn Bush Men’s Galloway Classic Chukka Boot

Nunn Bush Men’s Galloway Classic Chukka BootThe second pair of boots featuring on our list is the Men’s Galloway Classic Chukka boots by Nunn Bush. These feature more of a classic style, and are perfect for both workwear or casual.

  • 100% real leather
  • Classic appearance
  • Comfortable memory foam insole
  • Adjustable fit
  • High-quality rubber sole
  • Durable
  • These boots are not good in wet conditions.

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Nunn Bush are specialists in designing men’s fashionable footwear and accessories and have many years’ experience behind them. Therefore, you can be guaranteed a top-quality pair of shoes from them.

Perfect fit

Thanks to an adjustable four eyelet lace-up design, this ensures the right amount of adjustment around the foot, not too tight or too loose, and giving a more personalized fit to your foot.

Classic style

These men’s chukka boots are crafted using premium leather and suede which ensure a very comfortable and stylish shoe at the same time. They are available in 5 different colors, such as beige, dark brown, navy, tan and army green to give you a better choice.


If it’s comfort you are looking for in a men’s chukka boot, then these will do you proud. A high-quality foam insole is inserted into these boots which cushion every step you take. This also creates a custom fit and helps to relieve foot fatigue during the day.

Nunn Bush Men’s Chukka Boots

Dr. Martens Men’s Cabrillo Chukka Boot

Dr. Martens Men’s Cabrillo Chukka BootThe last pair of boots on our list is the Men’s Cabrillo Chukka Boots by Dr. Martens. These offer an iconic look and feature a nice sturdy design. We take a look at these Dr. Marten Chukkas in more detail below.

  • 100% leather
  • Cushioned sole
  • Rugged finish
  • Heat-sealed upper and sole
  • Iconic Dr. Martens yellow stitching
  • Slip resistant
  • The heels start to wear down after just 1 month

[Source]: We Thank Shop Zappos for the awesome video, and encourage readers to check out more videos and Subscribe to Shop Zappos


Dr. Martens is a brand which is known worldwide for their rebellious, distinctive styled boots and their chukka boot is instantly recognizable. These boots were inspired by the classic desert boots, and offer a sleek and simple design.

Lightweight design

As these boots have been inspired by the classic desert boots which were favored for their coolness and comfort in a warm climate, these two-eyed boots offer a lightweight construction which allows the wearer to feel like they are walking on air.

Iconic Dr. Martens look

If you are already a fan of Dr. Marten-style boots, you will automatically love these chukkas, as they feature the famous original yellow stitching which all other boots have as well as the thick, chunky sole which is extremely durable

Great slip-resistance

The best thing about these chukka boots is their anti-slip properties. Thanks to a strong construction, the sole offers good stability, resulting in a slip-resistant shoe which can be worn in almost all weather conditions.

CHECK PRICE of Dr. Martens Men’s Boots

Which are the Best Looking Chukka Boots?

So which are the best looking chukka boots? We think that all the chukka boots featured on this list are very trendy and also offer good properties, such as waterproof protection, extremely comfortable insoles or a classic, timeless look. It really depends on what you are looking for, but we guarantee there will be a pair to suit you.

If you are shopping on a budget and curious to find the most inexpensive option, the Nunn Bush Chukkas boots are fairly reasonably priced. The most expensive option is the Men’s Madson Chukka boots by Sorel.

We hope that this article has given you some inspiration to look for a new pair of men’s chukka boots, and hopefully you will soon find a stylish pair to wear.

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