Chukka boots are a classic footwear choice that every stylish man should have in his wardrobe. With their sleek, ankle-high design and versatile style, chukka boots can be dressed up or down to suit any occasion. 

In this article, we'll be sharing our picks for the 6 best chukka boot styles that every man should know about.

From casual, everyday wear to dressier options for special occasions, we've selected a range of chukka boots in a variety of colors and materials to suit every taste. 

What Is a Chukka Style Boot?

A chukka boot is a type of ankle-high boot that originated in the desert regions of North Africa and the Middle East. 

The name "chukka" comes from the game of polo, where it refers to a period of play. Chukka boots typically have two or three pairs of eyelets for lacing and a slightly rounded toe. They are usually made from suede or leather and can be worn with casual or semi-formal attire.

One of the defining characteristics of a chukka boot is its low profile. Unlike many other types of boots such as cowboy boots, which can be quite tall and heavy, chukka boots are designed to be lightweight and comfortable. 

This makes them ideal for everyday wear, as well as for activities like walking and hiking.

Another defining feature of chukka boots is their versatility. Because of their simple, classic design, they can be dressed up or down to suit a variety of occasions. They can be worn with a suit for a more semi-formal look or paired with jeans and a t-shirt for a more casual outfit.

Despite their simple design, chukka boots are extremely durable and long-lasting. They are often made from high-quality materials like leather or suede, which are known for their durability and ability to withstand regular wear and tear. 

This makes them a great investment for anyone looking for a versatile and long-lasting boot.

The 6 Best Styles of Chukka Boots

Here are the best chukka boots that will still be in style in 2023 and beyond: 

1. Clarks Originals Desert Chukkas

The Clarks Originals Men's Desert Boot is considered one of the best chukka boots for several reasons.

These classic chukkas feature Clarks Originals’ signature crepe soles and a convenient lace-up design. Available in a variety of colors, these timeless chukkas will never go out of style.

Notable Features 

• It is made by Clarks, a well-known and reputable brand that has a history of producing high-quality footwear
• The combination of leather and synthetic materials provides a high-quality, comfortable fit
• The lace fastening allows for a customizable fit and the crepe sole offers good traction and durability
• The fabric lining and eyelet trim add to the overall aesthetic of the boot, making it suitable for both casual and formal occasions

2. Frye Astor Chukkas

The Frye Astor Chukka is a contemporary chukka that offers a modern twist on a classic style. With a premium full-grain leather upper, waxed laces, and a rounded toe, these chukkas will add a stylish touch to any outfit.

Whether you're running errands or heading out for a night on the town, the Frye Astor Chukka is the perfect shoe for any occasion.

Unique Features

• The Astor Chukka is available in supple vintage pull-up leather and soft suedes, adding a touch of attitude to the classic Frye design
• It features a cushioned rubber outsole and a removable comfort footbed, which provides adequate support
• It has a 4" shaft and is leather lined for added durability and breathability
• Its imported design adds a touch of sophistication to this casual sneaker; made from premium materials and constructed to high standards 

3. Allen Edmonds Chandler Chukkas

The Allen Edmonds Chandler Chukkas are lace-up, chukka boots with a relaxed fit. 

These classic chukkas are crafted with Allen Edmonds’ signature quality and attention to detail. The upper is made from premium calfskin leather and features a brogue-style toe for a traditional look.

The history of these handcrafted leather shoes goes way back to the 18th century! The boots are designed to be everyday essentials that can be dressed up or down and are also eligible for recrafting by Allen Edmonds experts in the future.

Notable Things

• The boots have a 360º bench welt construction for durability and stability and are built on the 1757 footwear last
• They are handcrafted in Port Washington, Wisconsin with imported materials and feature premium, finely napped suede or Italian calfskin leather uppers
• They also feature a leather-lined interior and Dainite rubber soles that provide reliable traction while picking up less dirt
• The Chandler Chukkas also feature Custom Cork insoles that will mold to the unique shape of your foot

4. Red Wing Heritage Chukkas

These timeless Red Wing Heritage Chukkas feature a durable oil-tanned leather upper and Goodyear welt construction for long-lasting wear. The unique Speed Hooks lacing system ensures a snug and secure fit.

Things About Work Chukkas

The Work Chukka from Red Wing Heritage is a fan favorite for its exceptional comfort and stylish look. 

• The boot features a flexible Atlas Tred Polyurethane outsole, making it ideal for bending and kneeling without discomfort.
• It is built on a resole-able Goodyear welt with durable Puritan triple-stitch construction and nickel eyelets for lasting wear
• The Work Chukka is also made with the iconic No. 210 Last, a Red Wing last that was created in the 1950s for increased flexibility and lighter work
• The boot should fit comfortably tight on the foot, with enough room to wiggle toes, and Red Wing recommends trying on footwear in-store to ensure proper fit

Things About Weekender Chukkas

The Red Wing Heritage Weekender Chukka is a stylish yet comfortable boot with several notable features: 

• The boot is designed with lightweight, flexible stitch-down construction, which makes it comfortable from the moment it is put on
• The Hill outsole provides steady footing and a sleek look
• The No. 60 last has been specifically designed for stitch-down construction for the Weekender Collection and provides enough room for footbeds to adjust the fit
• The boot is ideal for warm-weather wear and can be worn with or without socks.

5. To Boot New York Boston Medium Brown Chukkas

These Boston Medium Brown Chukkas are designed with a sleek, contemporary silhouette and a rich leather upper. The flexible rubber sole ensures durability and style.

What’s Special About It

• These chukka boots are made with high-quality Italian suede, which is known for its durability and flexibility
• The boots also have a rubber sole that provides good traction and a leather lining that adds to their overall comfort
• Their medium brown color makes them versatile and easy to pair with a variety of outfits, from casual to dressy
• The matching med brown suede belt available is an added bonus, as it allows for a coordinated and put-together look

6. Cole Haan Men’s Original Grand Chukkas

The Men’s Original Grand Chukka is designed with a classic silhouette and a comfortable EVA midsole for all-day wear. The leather upper is made from premium full-grain leather and features a contrasting stitch detail for a stylish touch.

It's available in a variety of colors, ranging from classic black to bold brown. This chukka is the perfect addition to any wardrobe and is sure to be a staple for years to come. 

This shoe is perfect for a man who appreciates both classic style and modern design.

What’s Good About It

• The leather upper and storm welt make this chukka a timeless classic
• The storm welt gives the shoe a classic look, while the EVA midsole adds cushioning and support
• The rubber outsole offers superior traction and durability
• This shoe also features a luxuriously cushioned GRANDFØAM footbed for ultimate comfort and flexibility 

How to Choose the Right Chukka Boot Style for You

When choosing a chukka boot, it is important to consider factors such as personal style, occasion, and comfort. 

These factors can help you select a chukka boot that will best suit your needs and preferences.

Personal Style

The chukka boot is a versatile shoe that can be dressed up or down, depending on the occasion and your personal style. 

• For a more formal look, you may want to choose a chukka boot made from high-quality leather in a classic color, such as black or brown
• For a more casual look, you may want to choose a chukka boot made from suede in a more unique color, such as olive green or burgundy

Occasion

If you plan to wear your chukka boots to work or a formal event, you may want to choose a more formal style that is made from high-quality leather and features a sleek and polished design. 

For more casual occasions, such as a day out with friends or a weekend trip, you may want to choose a more laid-back and comfortable style, such as a suede chukka boot with a rubber sole.

Comfort

People normally buy chukka boots to wear for long periods, so it is important to choose a style that will be comfortable to wear. 

When trying on chukka boots, make sure that the boots fit snugly but not too tightly, and that there is enough room in the toe box for your toes to move comfortably. 

Additionally, consider the type of sole on the chukka boot, as a rubber sole will provide more traction and cushioning than a leather sole.

Where to Buy Chukka Boots

Chukka boots can be purchased from a variety of retailers, including shoe stores, department stores, and online retailers. 

Some popular shoe stores that sell chukka boots include Zappos, Nordstrom, and DSW. 

You can also find chukka boots at department stores such as Macy's and JCPenney, as well as online retailers such as Amazon and Zappos.com.

Additionally, many shoe brands have their own websites where you can purchase chukka boots directly from the manufacturer.

When shopping for chukka boots online, it is important to do your research and read customer reviews to ensure that you are purchasing from a reputable retailer. 

You can also look for deals and discounts, such as free shipping or special sales, to help save money on your purchase.

To avoid counterfeits, make sure to only purchase from reputable retailers, and check for any red flags, such as overly low prices or poor-quality images of the product. A good pair may cost you around $200-$500! 

It is also a good idea to read the product description carefully and check the return policy before making your purchase.

Chelsea Boots vs Chukka Boots

These two types of boots are often confused with one another as both are ankle-high boots. They both have a sleek, elegant silhouette and are versatile enough to be worn with both casual and formal outfits.

Chelsea boots like Veloce Chelsea Boot are characterized by their sleek, tight-fitting design, which includes a low heel and elastic side panels that make them easy to slip on and off. These boots were favored by the likes of the Beatles frontman, John Lennon.

Chukka boots, on the other hand, are typically made with two or three pairs of eyelets for lacing and have a more casual, rugged appearance. They are also often made with a higher heel and a thicker sole than Chelsea boots.

In terms of versatility, both Chelsea boots and Chukka boots can be worn with a variety of different outfits. 

Chelsea boots are a great option to pick for formal occasions, such as weddings or business meetings. They can be worn with a suit or dress pants for a polished and sophisticated look. 

Chukka boots, on the other hand, are a great option for casual occasions, such as weekend outings or running errands. They can be worn with jeans or chinos for a laid-back and comfortable look.

Conclusion

With their comfortable and durable design, chukka boots are sure to become a go-to choice in your shoe collection. These boots can easily be dressed up or down to suit any occasion. 

They’re also known for their comfort and durability. The low-cut design allows for easy movement and the sturdy construction ensures that they will last for many seasons to come.

Whether you're headed to the office or out on the town, a good pair of chukka boots can help you make a stylish and confident statement.

If you want to learn more about men’s boots, read this guide on the top 10 men's boots that never go out of style. 

FAQs

1. Are Chukka Boots Still in Style?

1. Yes, chukka boots are still in style. They’re often referred to as desert boots and are a timeless style that has been around for decades and continues to be popular today. They are a classic style that will never go out of fashion and will always be in style.

They pair well with jeans, khakis, trousers, and shorts, and look great with a blazer or sports coat.

2. How to Lace Chukka Boots?

1. To lace chukka boots, follow these steps:

• Start by threading the lace through the bottom set of eyelets on the boot, starting from the inside and going out.
• Next, cross the lace over the top of the boot and thread it through the next set of eyelets on the opposite side.
• Repeat this process, crossing the lace over the top of the boot each time and threading it through the next set of eyelets on the opposite side.
• When you reach the top of the boot, tie a knot in the lace to secure it in place.

Here is a video demonstrating the process.

Alternatively, you can use a different lacing pattern, such as the straight bar lacing pattern, to give your chukka boots a unique look. 

To do this, simply thread the lace through the eyelets in a straight line, going from the bottom to the top of the boot and back down again, without crossing the lace over the top of the boot. This will create a clean, symmetrical look.

3. Are Chukka Boots Good for Winter? 

1. Chukka boots can be a good option for winter, depending on the material they are made from and the type of socks you wear with them. Chukka boots made from leather or other waterproof materials can help keep your feet warm and dry in wet or snowy conditions. 

Additionally, wearing thick, warm socks can help to insulate your feet and keep them comfortable in cold weather. It's important to keep in mind, however, that chukka boots may not provide as much protection from the cold as more heavily insulated winter boots.