7 Best Chukka Boots for Men You’ll Love Wearing Daily

Daniel Bishop
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Chukka boots are a staple item on the feet of the winter-ready man. They pair perfectly with a wool flannel or wool pants and some heavy duty socks. And the best part is that you can wear them as a warm-weather option to your favorite chukkas.

So if you’re looking for a pair of the best chukkas for men for an upcoming fall wedding or you’re looking for the perfect winter boots you’ll love, this is a good resource for you.

But why chukkas?

Chukka boots are a style that is inspired by English riding boots. They feature a shorter shaft and have hosiery lacing for easy on and off. Chukka boots are popular for their comfort and more casual look. There are some great looking casual chukka boots out there that look great dressed up or down.

NameCategoryProduct
Timberland Men's EK Brook Park Chukka BootBest OverallTimberland Men's EK Brook Park Chukka Boot
Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka BootsBudget PickBruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots
Rockport Men's Rugged Bucks Waterproof BootUpgrade PickRockport Men's Rugged Bucks Waterproof Boot

1. Timberland Men's EK Brook Park Chukka Boot

Our rating: 9 / 10

Timberland Men's EK Brook Park Chukka Boot

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Pros:

  • They’re very comfortable
  • High-quality leather
  • Good feel and traction
  • Easy to get on and off
  • Waterproof
  • Great price for a high-quality product
  • Timberland provides great soles for these boots
  • They last for a very long time
  • They fit well and look good with almost all types of clothing

This time around, we’re talking about the Timberland EK Brook Park Chukka boot. One of the most affordable, highly durable, and fashionable pair of chukka boots on the market.

They’re built using high-quality thick leather that holds up well to daily wear and tear. Though not as much as a pair of all American-made boots. They’re lined with a synthetic material for added comfort and to enhance the waterproofing and protection.

The sole features a siped outsole giving it great traction and grip on almost all types of terrain.

2. Skechers Relaxed Fit Segment

Our rating: 8 / 10

Skechers Relaxed Fit Segment

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Pros:

  • You can choose from multiple color options
  • Great style and comfort
  • Easily worn for long periods
  • Very lightweight and flexible – great for everyday use

Skechers offers a variety of boots for men, but the Melego line has some of the most comfortable and stylish options.

If you’re looking for something fashionable with a relaxed and timeless appeal, the Melego is full in-step with the times.

It has a decorative strap across the front that gives this model a rugged, but still modern appearance.

3. Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots

Our rating: 8 / 10

Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots

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Pros:

  • These chukka boots are available in a variety of colors
  • The double stitching makes them durable
  • There’s a honeycomb rubber sole that will provide sure traction
  • You can wear these boots with casual outfits to make any outfit look great
  • You can wear them with a formal look as well.
  • The workmanship is superb; these are high-quality boots
  • They have the classic chukka style that will never go out of style
  • Wear them all day with no trouble because they offer excellent arch support
  • They’re made with premium suede leather, which means they’re expensive but worth the price
  • There’s a memory foam insole; you’ll feel like you’re walking on a cloud.

Cons:

  • There’s a tendency for the suede leather to get dirty easily
  • Fit may be a little snug, so you may have to order a half size bigger
  • These are boots that require some breaking in before you feel they are comfortable. But once they break in, you’ll wonder how you ever lived without them!

4. Clarks Men's Bushacre 2 Chukka Boot

Our rating: 8 / 10

Clarks Men's Bushacre 2 Chukka Boot

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Pros:

  • Very durable
  • Extremely comfortable
  • Excellent fit
  • Easy shipping

Cons:

  • Only comes in dark brown
  • Very hard-to-break-in

If you travel a lot, or are a working professional, it's best to own a pair of great chukka boots. As comfortable as they are convenient to wear, they'll be very helpful when deciding what to wear to the office. It's true that you can't go wrong with wearing chukka boots with a suit, but chukka boots will also look great with a pair of denim jeans for a more casual look.

We saw the need to prepare a list of the best chukka boots for men and found an excellent one to add to your home wardrobe.

The Clarks Men's Bushacre model was designed to offer quick and easy movement for all types of weather conditions.

5. Rockport Men's Rugged Bucks Waterproof Boot

Our rating: 8 / 10

Rockport Men's Rugged Bucks Waterproof Boot

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Pros:

  • Well-crafted
  • Good leather quality
  • Perfect for those who want to wear Chukka boots for more formal occasions as well
  • Provides a good amount of ankle support

Cons:

  • Not waterproof in heavy rain
  • Large fit so it might be a little roomy

If you’re looking for high-quality boots that will last you a long time, then the Rockport Men’s Rugged Bucks is worth checking out. It features a leather uppers, a rubber/leather outsole, moisture-wicking lining, and a compression-molded EVA midsole.

The leather is thick and sturdy and is bound to last you quite a while. The stitching is also sturdy, unlike other Chukka boots in the same price range.

6. Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots

Our rating: 8 / 10

Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots

Check Price on Amazon

Pros:

  • These chukka boots are available in a variety of colors
  • The double stitching makes them durable
  • There’s a honeycomb rubber sole that will provide sure traction
  • You can wear these boots with casual outfits to make any outfit look great
  • You can wear them with a formal look as well.
  • The workmanship is superb; these are high-quality boots
  • They have the classic chukka style that will never go out of style
  • Wear them all day with no trouble because they offer excellent arch support
  • They’re made with premium suede leather, which means they’re expensive but worth the price
  • There’s a memory foam insole; you’ll feel like you’re walking on a cloud.

Cons:

  • There’s a tendency for the suede leather to get dirty easily
  • Fit may be a little snug, so you may have to order a half size bigger
  • These are boots that require some breaking in before you feel they are comfortable. But once they break in, you’ll wonder how you ever lived without them!

7. Calvin Klein Men's Ulysses Suede Chukka Boot

Our rating: 7 / 10

Calvin Klein Men's Ulysses Suede Chukka Boot

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Pros:

  • 100% full-grain leather upper
  • Lace-up front
  • Padded collar for extra support
  • 100% man-made sole with rubber heel and toe

This is another chukka boot you’ll find to be on the pricey side, but that doesn’t mean it’s not worth the money. For starters, the upper is crafted out of 100% genuine leather. The lining and the insole are designed with genuine leather as well. And in case you’re wondering whether or not it’s durable, it’s tested to run for 10,000 steps without breaking.

Like with most chukka boots, it also features a flexible textile to help with support. And the print resistant rubber sole matches the brown color of the rest of the boots. And the lip at the top of the boots helps keep debris from getting in there.

It’s important to point out that the boots run 1/2 size small. So, if you normally wear a size 8, you should go with a size 8 1/2 instead.

Frequently Asked Questions (FAQ)

What color chukka boots should I get?

Chukkas are a classic boot for men and it would be rare to see someone wearing a pair of chukkas in a bright color. In general, men tend to wear chukkas in neutral colors like black or brown. It’s definitely possible to wear chukkas in brighter colors, but it’s not usual that you do.

As a result, it’s important to select a color that you feel completely comfortable wearing on a daily basis. For example, wearing chukkas in soft light brown or in the classic black will never go out of style. Those two colors will look great on any man. In any color, chukkas will instantly make you appear more mature and professional.

What are the best chukka boots?

Hmm, what’s the best chukka boot? That’s a great question. Truth be told, they’re all great. The best chukka boots for you will depend on your own unique needs. Consider the comfort features, the durability, the style, and the fit.

What matters most is that you have a boot that fits well and will look good regardless of what you wear it with. Many chukka boots tend to match nicely and compliment most outfits. This said, it’s always nice to have a choice of colors and patterns, so read the reviews and consider carefully what you might like to see not only this winter, but also in summers and in more formal seasons. And finally, remember that they’re boots, so it’s best to take good care of them.

Are mens chukka boots in style?

Mens chukka boots (also known as desert boots) have been a wardrobe staple for men since the 60’s. These popular shoes for men are exceptionally versatile and can be used for a wide variety of purposes. Like most boots, chukka boots can be worn in casual and semi-formal settings. They can be worn to work with jeans or with dress pants, and depending on how trendy you are, you may even wear them in more formal settings (such as a dinner date). The cool thing about chukka boots is that they are super comfortable and breathable. If you haven’t worn them for awhile, definitely consider adding these shoes for men to your style repertoire.

Although boots can be quite tall and thus very fashionable, the height of mens chukka boots is moderate, and they feature side zippers. A practical detail that shows up in chukka boots is the pull tab.

Can you wear chukka boots year round?

Yes, and you can wear them in just about any casual situation. They work well as a go-to shoe in summer when you want something stylish yet comfortable, and they are very versatile for winter, too.

Chukka boots are casual boots with a short height and a lace-up or zip-up design. For a lot of men, chukkas are their main footwear for all seasons. Provided that you get the right style for your foot and preferences, you should love wearing chukka boots daily.

Conclusion

You need to be comfortable when you’re wearing chukkas. If you’re uncomfortable (or boring), you’re going to ditch your shoes after a few hours. That’s why we came up with this guide. These chukka boots are comfortable, stylish, and well-made. Keep reading if you want to know more about them.

Our Recommendation

NameCategoryProduct
Timberland Men's EK Brook Park Chukka BootBest OverallTimberland Men's EK Brook Park Chukka Boot
Bruno Marc Men's Classic Original Suede Leather Desert Storm Chukka BootsBudget PickBruno Marc Men's Classic Original Suede Leather Desert Storm Chukka Boots
Rockport Men's Rugged Bucks Waterproof BootUpgrade PickRockport Men's Rugged Bucks Waterproof Boot