Chukka boots are one of the most versatile boot styles available. In fact, it’s quite possible you already own a pair or two.

They’re almost identical to desert boots and are frequently compared with Derby and Chelsea boots. They can, however, be challenging to wear properly due to their versatility and wide range of formality.

In this article, we’ll walk through what Chukkas are, how you can wear them, and some of the best models for sale on Zappos right now:

Beckett Simonon Ellis Chukka Boot

What Are The Best Chukka Boots For Sale On Zappos?

This section of our guide will help you find the best Chukka boots that are also currently available on Zappos. You can use the following menu to quickly jump between each shoe model or scroll down to take it from the top.

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What Are Chukkas?

Top And Side View Of Brown Chukka BootsA Chukka boot is a type of boot that typically extends to just below the ankle. They are usually made from premium leather or suede and have either two or three lacing eyelets.

Chukka boots originated in the UK, and are named after a game of polo played in short “chukkas,” or periods. Today, chukka boots are worn by both men and women and can be dressed up or down depending on the occasion.

Whether you’re pairing them with jeans and a tee for a casual look, or suits and dress shirts for a more formal outfit, chukka boots are a great choice. And because they come in so many different styles and colors, it’s easy to find the perfect pair to suit your unique style.

If you’re looking for a new pair of shoes to add to your collection, consider investing in a pair of chukka boots. You won’t regret it!

How To Wear Chukka Style Boots

Chukka boots are a great style of boot to have in your wardrobe. They are versatile and can be worn with many different looks. Here are some tips on how to style chukka boots.

Pair chukka boots with jeans for a classic look. This is a great option for everyday wear. You can dress up the look by adding a button-down shirt and sport coat.

Chukka boots also look great with khakis or chinos. This is a great option for business casual or weekend wear. Pair them with a polo shirt or sweater for a preppy look, or go for a more rugged look with a flannel shirt.

Beckett Ellis Chukka Boot On Feet Picture

Beckett Ellis Chukka Boots

If you want to get a little more dressed up, you can pair chukka boots with a suit. This is a great option for a night out or a special event. Just make sure the suit fits well and is in a dark color.

These are just some of the ways you can style chukka boots. Get creative and experiment to find the looks that work best for you. With a stylish pair of chukka boots in your closet, you will always be ready to look great and feel confident.

Shopping For Chukkas On Zappos

The volume and variety that makes Zappos a great place to shop for Chukkas (and any other style of shoe) can also make it slightly overwhelming. Indeed, when you’re faced with thousands of different shoes, picking the right pair for you can feel like a chore.

Zappos Category For Men's Chukka BootsFortunately, Zappos has integrated some very intuitive filter options on its user interface that will save you time when picking a pair of Chukkas. Most importantly for our purposes, they have an individual Chukka Boot category! To access it, simply click on “Men” in the top navigation bar on the homepage and then click on “Boots”. You can also use this link to get there directly.

Once you’ve sorted for Men’s Boots, use the search filters on the left-hand side of the page to select the Chukka Boot category. As you can see, as I’m writing this, there are nearly 500 different options available.

At this time, applying filters for your size, budget, preferred color, and even occasion is a logical next step. Yet, if you still feel overwhelmed, then check out the top Chukka boots on Zappos that we’ve picked out below.

1. Clark’s Bushacre 3

Clarks Bushacre 3 Chukka Boots
  • Color: Black, Navy, Taupe, Tan & More
  • Material: Waxy Suede, Beeswax, or Traditional Leather
  • Pricing: $110 $84 [Buy On Zappos]
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One of the brand’s most popular styles, the Clark’s Bushacre 3 represents the brand’s heritage. Famed for their desert boots listed below, their Chukkas such as these Bushacres feature all the traditional hallmarks of the shoe style. However, the Waxy Suede uppers conceal synthetic linings, a cushioned footbed, and a comfortable rubber sole.

2. To Boot New York Lamberto

To Boot New York Lamberto Chukkas
  • Color: Dark Brown, Slate Grey
  • Material: Italian Suede
  • Pricing: $350 [Buy From Zappos]
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Crafted from premium Italian Suede and available in both dark brown or slate grey, To Boot NY’s Lamberto Chukkas are not only sleek but also incredibly elegant. Up close, the excellent details shine, including the quality of the leather upper, the leather lining, contrasting welt, and the durable yet stylish rubber sole.

3. Johnston & Murphy Jameson Chukka

Johnston & Murphy Jameson Chukka
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Aside from the previous To Boot NY chukkas, which are quite exceptional, the Jamesons from Johnston & Murphy’s J&M Collection are also premium not only in their design but in their construction. Made in Italy, the Chukkas are equipped with a sporty Extralight rubber sole that not only ensures lasting comfort but also imparts a contemporary look.

We generally prefer the lighter tan color as it allows the phenomenal leather upper to weather and age as you wear it, giving the boots character over time. However, the blue leather upper with contrasting soles is also a great option.

4. Clarks Desert Boot

Clarks Casual Desert Boot
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Despite the fact that chukka boots are not technically chukka boots, they do share a lot of common characteristics. Untrained eyes cannot tell the difference between the two, in fact, they are nearly indistinguishable! With inspiration from the boots worn by British officers during the Second World War, these are very stylish boots for casual wear.

5. Carlos Santana Corazón

CARLOS by Carlos Santana Corazon Chukka Boot
  • Colors: Black, Brown
  • Material: Full-Grain Leather or Suede
  • Pricing: $154 $138.95 [Buy Now On Zappos]
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Carlos Santana’s modern interpretation of the chukka boot, the Corazón by Carlos Santana, is more than just a tribute to the legendary guitarist. With their Blake stitch construction, they are crafted from rich full-grain leather. Further, they are available in both black and brown leather, either full-grain or suede.

If you’re looking for a more formal pair, it’s best to stick with the Calfskin leather options. On the other hand, if you’re looking for a refined yet decidedly casual look, certainly give the suede version a try. With either option, you’ll get premium construction & materials in a sleek package.

6. Dr. Martens Bonny Chukka Boot

Dr Martens Bonny Chukka
  • Colors: Black
  • Material: Extra Tough Nylon
  • Pricing: $89.95 [Buy From Zappos]
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If you’re partial to the bulky and trademark Dr. Martens look but still want a Chukka boot, then consider the Bonny Boots.

These boast the sturdy construction and durability that characterizes Dr. Martens footwear while also remaining comfortable thanks to the lightweight sole (even if it doesn’t look light) and breathable upper. The pull loops at the back of the spine make them easy to put on and the lace-up system ensures a secure fit.

Lastly, and much like most Dr. Martens boots, the Bonny Chukkas have a cushioned footbed and air-cushioned outsole that is slip-resistant so you’ll stay on your feet no matter the surface your tread on.

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