Chukka Boots: Your Guide To Finding The Right Pair


Chukka chukka chukka chukka, despite the sound of this product’s name, the topic we’re covering today has nothing to do with trains. For those in search of some footwear that is simplistic, functional, and stylish, you’ll want to continue reading while we get into the nitty gritty and share with you everything you’d ever want to know about Chukka Boots.  I’m sure many of you have heard of Chukka Boots before but for those who haven’t, or need a refresher, here you go.

The Chukka Boot has been around since 1924 and was originally associated with and rumored to be worn by off duty British Soldiers who attended polo matches. The name Chukka, Chukker in Hindi meaning ‘circle’, references the 7.5min periods in a polo match and was where the iconic Chukka Boots got its name. After the Duke of Windsor wore them in the same year, the Chukka Boot gained attention and then quickly shot up in popularity in the 40s following the Second World War.

climbing the stairs in brown chukka boots
Nathan Clark, a former British soldier and heir to the Clark Shoe Company, caught on to the Chukka Boot and decided to introduced a similar product, the desert boot in 1949 at the Chicago Shoe Fair. These boots were an improvement on the original desert boot that were worn by British soldiers who were stationed in Egypt during the war. The high top, open laced boot they wore were of quality and versatility making them stand up to the harsh desert conditions of the area.

Throughout the years, the popularity of Chukka Boots has been steadily increasing and they have become a staple piece of footwear for many men all across the world. For a boot that is comfortable, built to last, stylish, elegant, and one that you can dress up or down, if you don’t already own a pair of Chukka Boots let me tell you, it’s a purchase you won’t regret making.

Now that you’ve refreshed up on your history of Chukka Boots, let us be your guide to everything you wanted to know and what to look for in a pair of Chukka Boots, maintenance of your Chukka Boots, what to wear them with, and finally we’ll offer up a list of the best Chukka Boots available on Huckberry right now!

Desert Boots vs Chukka Boots

Remember this one things – All desert boots can be classified as Chukka Boots but not all Chukka Boots are desert boots! Confused? Take a look at the comparative images below for a clearer understanding.

five features of dessert boots

A desert boot is simply a type of Chukka Boot. The difference between a desert boot and a pair of Chukka Boots is in the style & boot shape.

five main features of chukka boots

Features & Types Of Chukka Boots

If we were to generalize, we could call a Chukka Boot an ankle style boot but really they are so much more than that. They have 2 or 3 eyeholes, are made with leather soles and have thin laces. A smooth surface, subtle stretch, and beautifully built for versatility make Chukka Boots the ideal boot!

Let’s Point Out Some Distinguishing Features:

  • Rounded toe-box
  • Traditionally made of calfskin suede leather
  • Thin soles
  • Open lacing
  • Made from a single piece of leather

For a boot that is classic yet modern, stylish and comfortable, and a pair of footwear you can dress up or down, Chukka Boots really will be your answer to all your footwear conundrums.

When searching for the best pair of Chukkas, there really are a lot of great options out there so let’s just say, don’t settle for any old boot. Look for one that cannot only act as a dressy shoe but also allows you to wear it casually. For this look, search for a boot with open lacing and possibly a color scheme that is more casual such as one with brown shades rather than solid black or white. A rounded toe will add to the casual look of the shoe as well rather than a boxed toe.

Take a look below at some of the brands making the best types of Chukka Boots…

hudson logo

One of the most durable boots around made from strong leather and a multilayered sole. Best part about a pair of boots from Hudson are that you can actually afford them!

Red Wing Heritage logo

A brand that is trusted and worn by the outdoorsman who is looking for footwear that is stylish and with a heritage feel. Made in the USA since 1905. Red Wing Heritage uses oil tanned premium leather on all of their Chukka Boots which makes them water & stain resistant. Added Bonus: All boots are Goodyear Welted.

sperry logo

Known for being the boat boot, Sperry boots have a thicker sole which provides a great amount of comfort and support. They have a hand sewn moccasin construction and are designed with an Ortholite heel cup. Sperry Chukka Boots are lightweight, comfortable and have incredible cushion to them. Added Bonus: Enjoy the quality of the genuine rawhide laces on a pair of Sperry Chukka Boots.

timberland logo

If you’re looking for a boot that is smart, modern, lightweight and durable, you can’t go wrong with a Timberland boot. The best feature of these puppies is the incredibly high quality leather craftsmanship that is put into making each and every Chukka Boot.

astorflex logo

A brand you can feel good about supporting! Produced in Italy and known for making the best desert boots in the world, the quality of a pair of Astorflex boots comes out at the top. Astorflex aims to be the most sustainable shoe brand out there and does so by taking numerous steps to reduce the waste during manufacturing.

seavees logo

This United States brand could be summed up sum by saying that they are focused on comfort, casual, and quality. If you’re looking for a boot that is casual yet still of insane high quality, this may be the brand for you.

nisolo logo

Handmade in Peru from high quality cow hide which is sourced from local markets in Trujillo, you can’t get much more local and original than that. Every pair of Nisolo Chukka Boots is weather treated during the process as well so you can ensure your boots will be tough enough to withstand tough conditions. Another great thing about buying from the Nisolo brand is that you won’t be breaking the bank on your footwear purchase.

How To Keep Your Chukka Boots Looking As New

standing on wooden floor in brown chukka boots

There’s nothing worse than investing in a great pair of shoes only to see them get old and tattered long before their expiry. Chukka Boots will definitely stand up to some abuse but like anything, the better kept they are, the longer life you’ll get out of them. In order to extend the durability of this classic piece of footwear, you’ll want to keep them in top condition; this all starts with finding the proper shoe car items such as shoe polish for your Chukkas. It may seem obvious, but make sure you buy a polish that matches the color of your shoes.

If you’re unsure of which shoe polish to buy, try checking out this Kiwi shoe paste or Meltonion shoe cream. Kiwi has been a leader in the shoe polish industry for as long as many of us remember. The carnauba wax formula of the product allows it to permeate through the leather of your shoes to fill in scratches and remove any scuffs. For more of a luxury formula blend that is made with the finest of waxes, a Meltonion shoe cream is the way to go. He great thing about this product is that you can also use it on belts, purses, wallets and even on your furniture!

Remember: Never clean your shoes with a product that contains acid or detergent; they will age and damage your shoes.

Care for your Chukka Boots with these additional items:

What To Wear With Your Chukka Boots

A good pair of Chukka Boots shouldn’t only be for work; these boots are really a man’s best friend when it comes to go-to footwear. Pair your boots with cuffed denim or a pair of dress slacks or even a three piece suit. Whatever occasion you need to dress up or dress down for, we’re confident there’s a pair of Chukka Boots that’s just right for you.

If you’re not so style savvy here’s a few dos and don’ts when it comes to pairing your Chukka Boots:

Do Pair..

  • Crepe sole Chukka Boots with denim or chinos
  • Brows with fall trouser colors (greens and reds)
  • Casual clothes (ex.jeans or khakis) with canvas boots

Don’t Pair…

  • Crepe sole with dress pants or suits

Check Out The Top 6 Chukka Boots From The Huckberry Chukka Shop

chukka shop image from huckberry

1 – Greenflex – Stone (Astorflex)

stone Astorflex Greenflex boot from huckberry

These Astorflex Chukkas are available in Dark Chestnut, Dark Khaki & Stone, in addition to the Grey. Featuring a premium leather upper with an undyed leather line, 100% natural crepe rubber sole and soft suede lining, the characteristics make this boot a solid and reliable addition to your footwear collection. Described as one of the best desert boots in the world, these Italian made boots are responsibly made and boast to be 100% ecological. Flat and waxed round cotton laces are included and add that extra touch of style to the design.

BUY | $145

2 – Weekender Chukkas (Red Wing Heritage)

Hawthorne Muleskinner Red Wing Heritage Weekender Chukka Boot from Huckberry

Comfortable and easy to slip on, the design of these boots sticks to the truth of the name. The combination of Hill outsole, Texon Board insole, leather upper, and ComfortForce footbed ensures that a pair of Weekender Chukkas will provide you with that casual comfort you’re looking for.

BUY | $194.98

3 – Emilio Chukka Boot – Brandy (Nisolo)

brandy colored Nisolo Emilio chukka boot from huckberry

With inspiration taken from the original Chukka Boot, these boots which are handmade in Peru, mix tradition and modern effortlessly and can easily be worn to your upcoming business meeting or out for a drink on the town. If we had to describe a pair of Emilio Chukka Boots in two words, we’d probably use sophisticated and edgy.

The full-length, soft leather insole that has a built in arch support ensure that these boots are functional and comfortable along with being fashionable. Adding to the comfort, these classy boots have been designed with a microporous interior, lined with soft leather. For a secure fit, Nisolo has added a lace up closure which covers the ankle. The added layer of stitching between the upper and leather sole adds to a slightly rustic look that makes this boot versatile for many occasions.

BUY | $169.98 – $174.98 (Depends on color selection)

4 – Emilio Le Chukka Boot (Nisolo)

black Nisolo Emilio Le Chukka boot from huckberry

This limited edition version of the Emilio Chukka Boot has a pressed leather sole and is sleeker and slimmer than the original. Available in black exclusively, you’ll look your sharpest in this boot.

BUY | $119.98

5 – Original Chippewa

tan colored Original Chippewa boot from huckberry

These pair of dress Chukkas have been exclusively made for Huckberry. The American craftsmanship that has been put into each pair shows durability and extreme quality in make. Made with full grain American hide, Goodyear leather welt, Texon insole, and Vibram V-Bar outsole.

BUY | $199.98

6 – Luka Chukka Boot (Nisolo)

oak Nisolo Luka chukka boot from huckberry
Available in brandy, black, oak and steel, these Chukka boots are minimalist yet classic in design, have a modern toe and are the perfect pair of footwear for that classy or casual occasion. The internal elevated arch support along with cushioned leather insole will guarantee a comfort fit. Best part of owning a pair of Luka Chukkas is that you can feel good knowing that they are made in an ethical factory in Peru, where the employees are paid roughly 27% more than the fair trade minimum.

BUY | $174.98

 Want To Check Out More?

Huckberry features a huge selection of other styles and brands for all price points. If you didn’t fancy any of the Chukka Boots we’ve featured above, take a look at the link below for more.

Check here for a full selection of Chukka Boots from Huckberry

Chukka Related Videos


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