Written by Tanya Zhang

When the weather finally settles and cools and the first leaf starts to fall, I know it's time one of the best seasons of the year: fall. With the fall season arriving, I switch out my sandals and slides for a pair of ankle boots.

Seeing my partner with his year-round sneakers, I knew it was time to introduce some high quality chukka boots to his shoe rotation. I did my research online and gathered what guys on Reddit (and one of my favorite subreddits––/r/BuyItForLife) have bought and enjoyed, and compiled this list of the best boots so you didn't have to.

Along the way, I learned quite a bit about the chukka boot, its leather sole, and the best way to incorporate it into casual style. So, trust me, this list of smooth leather chukka boots won't disappoint.

 

What Are Chukka Boots?

Chukka boots are an ankle boot typically made from leather or suede, featuring two or three pairs of eyelets for lacing. They have a minimalist, sleek design that makes them a classic look for fall outfits and winter looks. The simplicity of the chukka boot is one of its strongest appeals, but don’t be fooled—this boot is anything but basic.

 

Why Are They Popular?

Chukka boots became widely popular due to their unique combination of comfort, versatility, and style. They can be worn with almost any outfit, from jeans and chinos to dressier slacks. The combination of casual and refined design makes them perfect for the modern man who values both fashion and functionality.

 

History of Chukka Boots

The origins of chukka boots are somewhat debated, but many believe they draw inspiration from desert boots "originally worn by British soldiers in the Western Desert Campaign of World War II" (Woolnough, Richard (2008-01-01). The A to Z Book of Menswear.)

These boots were lightweight, breathable, and sturdy—perfect for the rough desert terrain. Over time, this practical footwear became fashionable and was adapted into the sleek, stylish chukka boots we know today. In the modern fashion world, chukka boots have evolved from being military gear to one of the most versatile footwear options available.

 

Key Features

Materials Used (Leather, Suede)

Chukka boots are typically made from either leather or suede. Leather offers durability and can be dressed up or down, while suede provides a more casual, soft texture ideal for relaxed occasions.

 

Sole Construction

The soles of chukka boots can vary from traditional crepe rubber soles (as seen in the iconic Clarks Desert Boots) to rubber or leather soles. Each has its benefits; for example, crepe soles offer flexibility and comfort, while leather soles provide a more formal, polished look.

Lace-Up Design

One of the defining characteristics is their simple lace-up closure with two or three pairs of eyelets. This minimalist feature adds to their sleek appearance and ensures a snug fit. With nicer calfskin leather uppers, you'll find they break in more over time.

 

Why Chukka Boots Are a Wardrobe Essential

One of the main reasons chukka boots are so loved is their versatility. You can wear them with nearly anything in your wardrobe. Whether you’re aiming for a business-casual look or a chill weekend with friends, chukkas fit the bill.

They offer a perfect blend of style and practicality—something that’s hard to come by in men’s footwear. We recommend them as a must-have item for your fall wardrobe capsule.

 

How to Choose the Best Boots

Consider the Material: Leather vs. Suede

When choosing your pair of chukka boots, the material is one of the first things to consider. Leather chukka boots are durable and weather-resistant, making them ideal for year-round wear.

On the other hand, suede chukka boots offer a more casual, relaxed feel but require a bit more care, especially in wet conditions.

Look for Quality Stitching

Quality construction is key when it comes to these boots. Look for neat stitching along the seams, as this can be a good indicator of a well-made boot that will stand the test of time.

Assessing Comfort and Fit

They should feel snug around your foot but not overly tight. Look for boots with cushioned insoles or consider adding inserts if you need extra support. The crepe rubber soles found in some models, such as Clarks Desert Boots, adds extra comfort for long periods of wear.

 

Choosing the Right Sole Type

When selecting chukka boots, the type of sole is a critical factor that can significantly impact comfort, durability, and style. Here are some common sole types to consider:

Leather Soles

Leather soles are sophisticated and are often found in more formal chukka boots. They offer a classic look and can be polished to maintain a sleek appearance.

However, leather soles tend to be less forgiving on rough surfaces and may provide less traction in wet conditions. They are best suited for dry weather and semi-formal occasions where style is prioritized over ruggedness.

Rubber Soles

Rubber soles are a practical choice for everyday wear, offering excellent grip and durability. They are typically more slip-resistant than leather soles, making them ideal for various weather conditions. Rubber soles also provide a cushioned feel, enhancing comfort for extended periods of wear.

This type of sole is perfect for those who need a reliable option for casual outings or work environments where a bit of traction is beneficial.

Crepe Soles

Crepe soles, made from natural rubber, are celebrated for their exceptional cushioning and shock absorption properties. They provide a soft, flexible feel, making them ideal for long days on your feet.

While they may not have the formal appearance of leather soles, they add a unique character to the boots and can be dressed up or down with ease. Crepe soles are especially great for casual wear and urban exploration, as they offer good traction while keeping your feet comfortable.

 

Consider Goodyear Welt Construction

When it comes to durability and repairability, Goodyear welt construction is a hallmark of high-quality boots. This method involves stitching the upper part of the boot to a welt, which is then attached to the sole.

This creates a strong bond that not only enhances durability but also allows for easier resoling. This means you can extend the life of your chukka boots significantly by having them refurbished rather than replaced. Additionally, the Goodyear welt design offers a slightly raised profile, contributing to a more comfortable fit by allowing for better airflow and moisture management.

 

How Much Should You Spend?

The price of these boots can vary widely depending on the materials, craftsmanship, and brand. For a decent pair, you should expect to spend between $100 and $300.

• Budget Range (Under $100): You can find basic chukka boots in this price range, often made with synthetic materials or lower-grade leather. While they can be stylish, they may lack durability and comfort. (Trust me when I say I've bought several pairs in this category, and it is just not worth it.)

• Mid-Range ($100 - $200): In this range, you'll find well-crafted chukkas made from genuine leather or suede. These boots offer better quality, comfort, and durability, often with features like cushioned insoles and sturdy outsoles.

• Premium Range ($200 and Above): Premium chukka boots often feature high-quality materials such as full-grain leather, suede, or Goodyear welted construction. These boots are designed for longevity, and while the initial investment is higher, they provide excellent value due to their durability and ability to be resolved.

Depending on your outfit goals and budget, you can find a pair of boots that will meet all the requirements in terms of their looks and overall aesthetic. The comfort and durability of these chukka boots will be another topic. But we gather a few options in the upcoming section so you can find the right style chukka boots for you.

 

Top 5 Best Chukka Boots for Men

1. Clarks Desert Boots

 

 

We had to start the list off with the CDB, or Clarks Desert Boot. Why? They're a classic in men's shoewear and one that endless customers have raved about. If you’re looking to upgrade your style without breaking the bank, chukka boots are an excellent investment.

They strike a perfect balance between quality and cost, making them ideal for anyone stepping into the world of men's fashion. When it comes to soles, CDBs typically feature crepe soles, like the Clarks Bushacre models. Crepe soles conform to your feet over time, providing unmatched comfort after the break-in period.

 

 

However, these are not the best waterproof shoes due to how they're constructed. So if you're looking for a chukka boot that leans more practical and live in rainy conditions, I'd skip this one. Besides that, many reviewers claim to have had the CDBs for decades and enjoy their overall look even after the wear and tear.

 

2. Thursday Boot Co. Scout Chukka

Thursday Boot Co. quickly gained recognition for its stylish service boot designs and has since become a standout name among online brands. The company now offers an extensive selection of leather products for men and women, including sneakers, dress shoes, and outerwear.

 

 

Reviewers highly regard their customer service but it'll be rare to find their desert boots at a discount. However, you can still find some of the most competitively priced Goodyear welted desert boots crafted from premium materials like Horween leathers and shell cordovan.

We've seen them around and always hear them as being a highly regarded desert boot brand.

 

3. Johnston & Murphy Copeland Chukka

The Johnston & Murphy Copeland Chukka boot comes up a few times across forums as a super comfortable chukka boot that won't hurt your feet. It's a highly rated chukka boot that promotes premium, water-resistant leather or oiled suede. 

This chukka boot has sheepskin lining and memory foam cushioning, all with a genuine crepe rubber sole. The sheepskin lining offers luxurious comfort, natural temperature regulation, and moisture-wicking properties, keeping your feet warm, dry, and fresh.

Memory foam cushioning provides personalized support by molding to your foot’s shape, relieving pressure, and absorbing shock for all-day comfort. The genuine crepe rubber sole enhances flexibility, offers excellent traction on various surfaces, and provides superior shock absorption while being highly durable for long-lasting wear.

Some reviewers say they're comparable to some chukka boots from Thursday Boot Co but are far more comfortable. They currently retail for $175 but you can come across some deals that get the price down to $99. The other Johnston & Murphy chukkas are just as popular so you can't go wrong!

 

4. Allen Edmonds Chandler Chukka Boot

 

 

While the Dundee 2.0 from Allen Edmonds has been a popular choice for fashionable guys looking for a reliable chukka boot, it's been retired. I couldn't do a boot list without including Allen Edmonds. We've personally been a fan of AE's high-quality leather and construction. While Allen Edmonds sits at a higher price point, they often provide factory seconds or pre-owned shoes at a hefty discount.

 

 

Crafted from the finest materials, these Chandler chukka boots feature the signature 360° Goodyear bench welt construction which allows their experts to refurbish them when they start to show wear. Inside, the leather-lined interior offers a luxurious feel, while the Dainite rubber soles are engineered for reliable traction, minimizing dirt pickup.

Additionally, the CustomCork™ insoles mold to the unique shape of your foot for personalized comfort. I like that they also have a dark brown option as well as a suede upper to choose from.

 

5. Red Wing Heritage Weekender Chukka

 

The Red Wing Heritage Weekender Chukka stands out as one of the top chukka boots for men. Made in the USA, these boots embody the heritage and tradition that Red Wing is known for, using premium materials that ensure durability and longevity.

The leather upper is not only visually appealing but also develops a unique patina over time, making each pair truly one-of-a-kind. This attention to detail in materials and construction elevates the Weekender Chukka above many competitors, solidifying its place among the best.

The Red Wing Heritage Weekender Chukka features a durable hill outsole designed for excellent traction and stability on various surfaces. Its stitch-down construction enhances flexibility while ensuring a secure fit, providing comfort during long wear. Built on the 60 last, this boot offers a slightly roomier toe box, accommodating different foot shapes.

The upper is crafted from high-quality nubuck, oiled, and waxed leather, which not only enhances its rugged aesthetic but also provides water resistance and durability. While it doesn’t have a shank, the boot remains lightweight and comfortable, and it is resolable, allowing for extended use and sustainability.

 

How to Style Chukka Boots

Styling Chukka Boots with Casual Outfits

Chukka boots are incredibly versatile and can be styled effortlessly with casual outfits. For a laid-back look, you can easily throw on a pair of chukkas with your favorite jeans and a simple tee. They're a great shoe to dress up jeans for a business casual look.

If you're looking for an extra layer, consider adding a lightweight sweater or a casual button-up shirt. Opt for neutral or earth tones in your footwear to keep the outfit cohesive and allow for easy mixing and matching. You can also experiment with different denim washes—light wash for a more relaxed vibe or dark wash for a slightly dressier look.

Accessories like a canvas belt or a stylish watch can further elevate your ensemble without making it feel overdone. Here's how to find the right belt size and how to wear a watch.

 

Pairing Chukka Boots with Formal Wear

While chukka boots are often associated with casual attire, they can certainly hold their own in more formal settings as well. Try a pair of sleek leather boots in shades like black or dark brown chukka boots when dressing up.

These colors are perfect for a semi-formal look and pair beautifully with tapered trousers and a crisp blazer. Try one of these best blazers we recommend. Choose tailored dress pants in a complementary color and a slim fit dress shirt. Read this guide on how to wear a suit with boots.

 

Adding a slim tie or pocket square can elevate the outfit even further, giving it a refined touch suitable for events like business conferences, weddings, or upscale dinners. When wearing chukka boots in a formal setting, it’s essential to ensure they are clean and well-maintained, as the condition of your footwear can significantly impact your overall appearance.

 

Styling Tips for Different Seasons

Chukka boots are remarkably adaptable, making them suitable for year-round wear. In the summer months, you can pair them with light chinos or shorts for a breezy, casual look. Opt for breathable materials to keep your feet comfortable during warmer weather.

Light-colored chukkas, such as beige or tan suede, can add a summery touch to your outfit. Consider wearing them with a short-sleeved button-up shirt or one of your favorite polo shirts to maintain a smart casual vibe.

As the temperatures drop in the colder months, chukka boots transition seamlessly into your winter wardrobe. They pair well with denim or wool pants, providing warmth and comfort without sacrificing style. For added warmth, consider wearing thicker socks, which can also add a cozy aesthetic when peeking above the boots.

Layering is key in winter, so a stylish overcoat jacket or a chunky knit sweater can complete your look while keeping you warm. Whether you're heading out for a casual lunch or braving the cold on a city stroll, chukka boots can be the perfect finishing touch for any seasonal outfit.