Chukka boots burst upon the scene nearly a hundred years ago. A traditional yet hip design, these classics are a staple footwear for men of good taste. And like any timeless style, the chukka’s got a sweet backstory.
Chukkas are typically leather, ankle-high boots featuring an open lacing construct with a few pairs of eyelets. The word “chukka” comes from a Hindi term chukkar — in the game of polo, a chukka refers to a seven-minute period of play. One complete polo match consists of four to eight chukkas. Although polo players didn’t actually play in chukkas, the boots were the preferred after-match loungewear.
The history of the chukka — sometimes called a desert boot — is a little fuzzy. It’s likely the first chukkas were worn in India by off-duty British soldiers. In 1924, the Duke of Windsor wore chukka boots in the United States, and the fever began. After WWII, shoe company Clarks launched the chukka into the popularity it still enjoys today.
Ready to score a pair of chukkas for yourself? Let’s take a look at 15 of the best men’s chukka boots for casual and formal wear.
Red Wing Weekender Chukka
Since 1905, Red Wing Heritage has made quality shoes in their home base of Minnesota. The 3326 Weekender Chukka is perfect for your next adventure, from a new coffee shop to a day on the hiking trails. Crafted from Red Wing’s signature Red Maple Muleskinner roughout leather, it’s comfortable and durable.
The leather is created in-house at S.B. Foot Tanning Co. with a reverse-suede technique. The hide doesn’t split, which equals a longer life for the shoe.
Wear this boot with or without socks — it won’t rub. It’s lightweight, too, so the Weekender won’t weigh you down. The boot is built around a shoe last that contains a removable footbed and a snug construct.Check Current Price
Red Wing Work Chukka
This sleek copper boot is described as an “indoor work boot,” but the shoe is more supple and aesthetically pleasing than what you’d normally think when you hear work boot. Red Wing makes the 3137 Chukka with an Atlas Tred sole, Rough & Tough oil-tanned leather with a three-eyelet lacing system, and triple-stitch seaming.Check Current Price
Clarks Desert Boot
The iconic Clarks Desert Boot is made in Italy with suede from England, and available worldwide. The luxury Bronto suede is high-quality and durable, and the shoe has a full runner board with Clarks Originals crepe rubber.
Clarks Shoes prides itself on innovative technology and creativity. Their Desert Boot fastens with laces and does not include a removable insole. It comes in thirteen colors, from natural tan leather to the classic black suede to a versatile olive.
It’s a relatively expensive shoe, but you get what you pay for, and the durable sole should last years. The Clarks Desert Boot is a comfortable classic offering plenty of support.
The leather resists water, stain and perspiration. Plus, it’s durable, and the color is bright and vivid — the leather was given only a minimal treatment, so it still looks natural. This boot is perfect for indoor jobs where you need a lightweight boot that moves with your foot: the sole is flexible and won’t scratch a wood floor.Check Current Price
Danner Wolf Creek Chukka
Danner’s dark brown chukka boot is shiny, supple, and versatile: it can go with just about any outfit for any casual event. The boot is inspired by a traditional work boot pattern, staying true to the clean and simple lines, but with a little extra style and pizzazz.
The lining is waterproof — moisture can escape, but no water will come in — and the Vibram outsole is comfortable while giving your foot extra stability. The full-grain leather is extremely durable as it’s subjected to six separate tests before being used for the shoe.Check Current Price
Frye Ashland Chukka
The price of this chukka boot may be on the steep side, but it’s worth the price. Frye created this versatile boot with full-grain Buffalo leather, and the stitching construction is projected to last for years before needing repairs. The leather lining is comfortable and smooth so your foot won’t rub.
Frye is an American heritage brand founded in 1863 and have since placed a high priority on creating well-crafted leather goods. Lightweight and supportive, the Ashland is practical and still stylish.
The leather is well-made, equaling a good return on your investment. Try the Ashland on for size for anything from a day at the office to an adventure in the woods.Check Current Price
Thursday Boot Company Scout
Described as “the chukka for a new generation,” this boot blends simplicity and style. Round wax laces give the shoe a minimalist look, and a full glove leather lining creates a soft environment for your foot.
The stitchout construction keeps water out, and studded rubber outsoles add ample traction so you won’t slip. The Scout also features a beautiful WeatherSafe suede upper and a cork footbed that forms to your foot.
The Scout comes in a myriad of colors: honey suede, dark olive suede, glazed ginger, caramel, black suede, midnight suede, cognac suede, and brown. Thursday Boot Company also offers free domestic U.S. ground shipping.Check Current Price
Cole Haan Wagner
The Wagner Grand Waterproof Apron Chukkas come in four shades of waterproof leather: black, java, mesquite and midnight waterproof nubuck (a cowhide leather that feels like suede).
The trademark feature of this chukka is its comfort. The shoe sports Grand.ØS energy foam to provide cushioning during a long day on your feet, and the footbed is bound in leather as well.
The waterproof leather and GrandGrip leather sole with GrandControl traction make this boot safe for any kind of weather. It’s both a flexible shoe and a durable one while maintaining a lightweight feel. The Wagner is well-constructed and ready to take you places.Check Current Price
Johnston & Murphy Copeland Chukka
The Copeland Chukka is made of either water-resistant leather or oiled suede with a soft sheepskin lining, supportive memory-foam cushioning, and a crepe rubber sole. Color options are varied: choose from gray oiled suede, tan oiled full grain, black tumbled full grain, taupe oiled suede, red brown oiled full grain, or navy oiled suede.
Apparel company Johnston & Murphy launched in New Jersey in 1850. The company likes to reinvent the classics, and they’ve made a habit of creating shoes for every president since Millard Fillmore. The Copeland is no exception to the company’s classic trend; it’s simple, stylish, and ready to go.Check Current Price
To Boot New York Banker
To Boot New York values style, quality, and comfort, and the Banker chukka has all three. The lacing system is a two eyelet stance that sits up high, giving the shoe long lines. The rubber sole is 100% pure gum for extra comfort and durability.
The boot comes in a taupe color that goes well with any shade of gray, tan, or blue. It runs large, and the website advises customers to purchase the next size down.Check Current Price
Nisolo makes handcrafted and ethical leather shoes and accessories. The stylish Luca has minimalist leanings: an updated design includes fewer eyelets, sleek lines, and a modern toe. This boot works for all seasons, but for maximum durability, Nisolo advises against wearing it in the rain.
You’ve got four color options with this chukka: brandy, black, oak, and saddle brown. The Luca has extra arch support and leather lining. The shoe is comfortable and well-made — you’re getting a good value for your money here.
To put a cherry on top, this chukka boot is ethically made in Peru. According to Nisolo, their producers receive “beyond fair trade wages, healthcare, and a healthy working environment.”Check Current Price
This eco-friendly desert boot is handmade in Italy, created by a six-generation family of boot-makers. The Greenflex is made with premium European leather and aged for thirty days in a mixture of oak bark, water and powdered mimosa. Next, natural ingredients are used to soften the leather, and the design is topped off with natural rubber soles.
Comfort and style energize this chukka. The footbed is ergonomic — specifically designed for comfort. Parent brand Huckberry creates a variety of products, but its Astorflex footwear collection is stylish, eco-friendly, and comfortable.Check Current Price
Oak Street Bootmakers Natural Campus
Oak Street Bootmakers create shoes handcrafted in the USA by experienced cobblers, and with the Natural Campus, you pay for their experience. Although more expensive, this chukka has a long list of exciting components: oiled leather Waterlock soles, a stacked leather heel, and a deerskin lining.
The shoe runs true to size, and the company advises a snug fit since the shoe will stretch. The Natural Campus is built on Oak Street’s Elston Last, giving the shoe a solid structure. Horween Chromexcel leather is soft and durable, and the deerskin lining adds an extra level of comfort.Check Current Price
Brooks Brothers Field Chukka Boots
At 200 years old, Brooks Brothers is the USA’s longest-tenured clothing retailer. The company makes a point to not only put out great products, but also to partner with nonprofits and make a difference.
The Field Chukka is made from suede and crafted in Italy. Featuring tonal stitching, a leather lining, and a rubber sole, it comes in five colors: black, brown, light brown, tan, and navy. The shoe is smooth, comfortable, and versatile – everything you want in a solid chukka.Check Current Price
Wolf & Shepherd Striker Chukka
The stylish yet rugged Striker is a rebel, full of contradictions. A minimalist design, it still manages some exciting features. It’s made of soft leather, but contains a sturdy carbon fiber shank.
In keeping with the Wolf & Shepherd tradition, this chukka is “ridiculously comfortable.” Described by Wolf & Shepherd as “pushing what is possible,” the Striker is comfortable, water-resistant, and oozing with style. Available in two colors — chocolate or bullet — the shoe is a pound lighter than other dress shoes and is made in Portugal.
It incorporates many features similar to those of athletic shoes, such as a dense EVA foam heel, sturdy outsole, and heel-to-toe ratio adapted from a running shoe. You can even resole the Striker with tread patterns specifically meant for summer or winter.Check Current Price
Taylor Stitch Chukka
Taylor Stitch’s chukka boot comes in chocolate suede and is completely waterproof and weatherproof — don’t worry if you tend to scuff up your shoes, because with this chukka, it’ll just add to the aesthetic.
The deerskin lining and foam insole make the boot extremely comfortable. Handmade in Leon, Mexico — the shoe making capital of the world — it offers a resoleable construction for an impressive price.
Taylor Stitch takes their shoes seriously: each chukka is made from twenty individual parts stitched together with one thousand stitches. The company’s attention to detail lets you enjoy a shoe that will last for a lifetime.Check Current Price