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    How to Wear Chukka Boots (Must-read Style Guide for Men)
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How to Wear Chukka Boots (Must-read Style Guide for Men)

Looking for Chukka boots outfit inspiration? Wanting to expand your closet with a pair of classic shoes? Let us help you navigate how to wear Chukka boots below.

If you want to elevate your casual attire, Chukka boots are the way to go. In other words, a good pair of Chukkas allow you to maintain a sense of style and a comfortable feel. The iconic boot is a worthy addition to any closet.

History of Chukka Boots

The origin of Chukka boots is somewhat of a mystery. Shoe historians agree Chukkas became popular in India and receive their name from a period of play in a polo match. In the 1920s, the Duke of Windsor wore a pair to the U.S. after spending time in India, and for his interest in polo. Chukkas also closely resemble riding shoes such as the jodhpur and Chelsea boots.

Later in the 1940s, a variation of chukkas emerges called Desert boots. Desert boots feature crepe-soles and suede uppers. The style is a nod to a South African shoe called veldskoen. C. and J. Clarks shoe company later popularized the Desert boot, and indeed Clarks is still one of the leading manufacturer of Chukkas to this day.

Chukkas subsequently became popular amongst the mods in the UK and the rude boys of Jamaica. Members of both movements were wearing them as a casual, yet sophisticated shoe. Chukka boots are so strongly associated with the rude boy movement that if someone was seen wearing the shoes, they would instantly be IDed as a member of the subculture.

In 1990s New York City, the popularity of chukka boots saw a revival by the rap scene at the time. Wu-Tang Clan is notorious for their love of Chukka boots, specifically a style called Wallabees. Members have music, nicknames, and shoe design collaborations memorializing Chukkas. Ghostface Killah even has a 2008 album titled “The Wallabee Champ.”

Anatomy of Chukka Boots

There are many variations of Chukka boots, but several key features make up the design. The boots feature two to three eyelets, a rounded toe, thin laces, thin soles, and come to ankle height.

Desert boots and Wallabees are types of Chukka boots but have notable differences from traditional Chukkas. Desert boots are a more casual version of Chukka boots and feature thicker soles. Wallabees have the iconic silhouette but have a flat heel.

Chukka boots can come in suede or leather, and come in a variety of colors. Suede is the most common material and is a great option to add texture to your look. Leather chukkas provide a more elegant feel.

When and Where to Wear Chukka Boots

Chukka boots:

  • are fairly versatile, with a long history of having both elegant and casual vibes. Chukkas also come in a variety of colors making it easy to mix and match your boots with many outfits.
  • are perfect for (almost) any season. Unfortunately though, they don’t fare well in icy, wet weather. Some manufacturers design waterproof, insulated Chukkas to counter this. Winterized Chukkas often stray from traditional elements and might be too casual.
  • aren’t the most formal ankle boot options to choose from. If you’re wanting to pair Chukkas with a suit you’ll want to stick with a darker leather. You’ll want to cover the tops of your boots with the leg of your trousers. The loose look of the ankle doesn’t convey the most professional air when comparing Chukkas to other shoes.
  • look excellent with a pair of chinos or jeans. A camel color pair of Chukkas is flattering against a dark wash denim or a pair of army green slacks. A darker brown or grey pair of Chukkas will compliment navy or black slacks.

The variety of colors allows for experimentation. Roll up your pants legs to show off the silhouette. Buy multiple colors to match many occasions and outfits. Have fun with it. Chukkas are a timeless boot for a reason.

Related Reading: Oxford Shoes Guide

How to Maintain Chukka Boots

Since Chukkas are so versatile and timeless, you’ll want to invest in a solid pair. You can learn to take care of your boots in order to have them around for years to come. Luckily, you don’t need to spend a fortune to obtain a high-quality pair of Chukka boots. They feature a simple design that uses only a small amount of material, which can keep costs low.

Suede vs. Leather

Leather Chukkas are easier to maintain, as leather is more durable than suede and can be cleaned with ease. Some leather boots will come waterproof, making maintenance a breeze. Although, you’ll want to avoid water and rough terrain if your Chukkas have a leather sole. Reserve boots with a thin, leather sole for a more formal setting.

The leather upper of Chukkas will need to be buffed occasionally in order to keep it conditioned and free of any scuffs. A shoe brush and leather polish will do the trick; weatherproofing sprays are a good choice if you plan to frequently wear your leather Chukkas outdoors.

Suede is going to be more sensitive than leather. Scuffs on suede are more common, and your shoes will need to be frequently checked for any wear or stains. Water is a major culprit when it comes to ruining a pair of suede shoes. Suede is more porous than leather and when it gets wet, stains set fast.

Try to brush or wipe away dirt from your suede Chukkas with a suede brush. A mix of water and vinegar can be of use when removing stains. Make sure you avoid using too much liquid and soaking the boots. Once your boots are clean, let them dry and brush away any remaining dirt. If you’re wearing them in the snowy winter months, a water and vinegar mix is also helpful to remove salt stains.

Chukkas are a soft, malleable shoe. There is always a chance of bending the upper or the toe getting squished. To avoid any unpleasant creases or dents, look into purchasing a shoe tree. Shoe trees are primarily made out of wood and help to not only hold the shape of shoes and boots, but they also fight odor.

How to Choose a Pair of Chukkas

With so many options to choose from and almost every shoe company producing some variation of chukkas, it can be overwhelming to find the right ones for you. We want to help you out in the process and came up with a small list of popular Chukkas.

1. Velasca Umbrelee Desert Boots

Velasca Umbrelee Desert Boots Shop Now

Dressing for a fancy occasion or getting ready to stand in the mud for hours on end? This pair of boots are comfortable and stylish no matter what you pair them with, no matter where you wear them. Velasca has been making premium Italian footwear without the usual premium prices. You can expect this Milanese label to deliver in terms of quality, sophisticated style, and comfort. And that’s what you get from the Umbrelee desert boots, their streamlined version of the classic and functional Chukka boots. 

It’s another winner that gives you exactly what you would expect from boots made in Italy – excellent leather material, high-standard craftsmanship, and a pair of boots designed to look great and feel great. Chukka boots by Velasca features suede calf leather with Vacchetta leather lining and para rubber sole and heels. 

Promising to be the most casual boots, this pair offers impressive versatility and flexibility. Think casual lunch on weekdays and leisurely day outs on weekends.

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2. UGG Men’s Neumel Boot

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UGG might be famous for their signature sheepskin boot, but they deserve to be known for their Chukkas as well. The Neumel chukka boot features a flat heel, wool insulation, and Treadlite soles. UGG boasts that their signature UGGpure wool insulation can keep your feet warm in the winter and keep your feet dry in the summer.

Treadlite soles offer better cushioning, traction, and durability when compared to other EVA outsoles. UGG Neumel Chukkas come in a plethora of colors and you can purchase them in both suede and leather. Neumel Chukkas are best for casual wear.

3. Clarks Bushacre 2 Chukka Boots

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Clarks is instrumental for making Chukka boots what they are today. The company is famous because of the classic boots. Bushacre 2 Chukka boots are quintessential examples of the boots timeless silhouette.

Bushacre 2 Chukkas feature two eyelets, thin laces, and a thin rubber outsole. The thin outsole is durable and lightweight because of the rubber. The Bushacre 2 boots are textbook Chukkas. You can buy a pair of Clarks Chukka boots in a variety of colors, and easily enhance your wardrobe.

Bushacres come in suede, smooth leather, and brushed leather. The brushed leather options available make it easier to maintain your boots as they will already appear distressed.

Due to their traditional design, Bushacre 2 Chukkas are a good neutral boot when comparing them to the UGG Neumel. Leather Bushacre 2s pair well with casual or more professional clothing. The suede and brushed leather boots will add texture and edge to a more casual look.

4. Bruno Marc Men’s Suede Chukka Ankle Boots

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Bruno Marc is a relatively new company that has been manufacturing shoes since 2013. Since then, Bruno Marc has made it their mission to design quality, affordable men’s shoes without sacrificing style. The company produces shoes for business, business-casual, and casual occasions.

Chukka boots by Bruno Marc have 3 eyelets, a thin lace, and rubber outsoles. Bruno Marc Chukkas are an attractive boot that lies somewhere between the UGG Neumel, and Clarks Bushacre 2. Bruno Marc Chukka boots are only available in suede, and not smooth leather. So, this pair of Chukka boots is best reserved for business-casual occasions.

Be mindful of the condition your Chukkas are in and clean any dirt or scuffs. Of course, Bruno Marc shoes are affordable, which takes away the pressure to perform shoe maintenance.

Final Considerations

After reading over our breakdown of how to wear Chukka boots, you should be ready to move forward and add this uniquely attractive boot to your closet. If you’re wanting to look sharp on the weekends, or pay homage to the NYC rap scene, Chukka boots are a must have.

Have any other recommendations of great Chukka boots or how to style them? We would love to hear from you in the comment section below.