16 of the Best Chukkas for Men to Dress up Those Jeans and Chinos

You’ve come to the right place if you’re looking for some of the best chukkas for men anywhere. Chukkas are such a great shoe because they bridge the gap between smart casual and dressy in an effortless way. You can dress them up with your favorite navy blazer and tie. Or dress them down with a great pair of slim jeans and chinos and a t-shirt. Whatever your choice men’s chukkas will only improve the outfit.

J. Crew Macalister Boot in Suede

The J. Crew Macalister Boot in Suede ($150) is one of my favorite men’s chukka. It comes in at a great price point, is available in great colors, and is durable. These crepe-sole boots were inspired by the boots worn by British officers during World War II. They’re made from Italian suede and only get better with age. They’re unlined so you can easily wear them in hotter months, or layer them with wool socks in the fall.

Red Wing Heritage Men’s Work Chukka

If you’re looking for a shoe that’s built like a tank, look no further than the Red Wing Heritage Men’s Work Chukka ($185). The Heritage Chukka features a 100% leather upper and a leather sole. The boot shaft measures four inches from the arch and has about a one-inch heel. Additional features include three nickel eyelets and an Atlas tread sole. Of course this awesome boot is 100% Made in the good Ole U.S. of A.

Clarks Men’s Desert Chukka Boot

If you’re looking for the Godfather of Chukka boots, you’ll want to check out the Clarks Men’s Desert Chukka Boot ($117). Clarks has been in business for over a 100 hundred years and they’ve been making their version of the Desert boot since 1950. When it was introduced by Nathan Clark. The boot features a 100% suede leather upper, with a 4.25″ shaft. It sits on a classic slip resistant crepe sole with a stabilizing heel counter. If you want a great boot at a great price point look no further than the Clark Chukka.

Thursday Boot Company Scout Men’s Chukka Boot

The Thursday boot company says they focus on delivering the highest quality products with best-in-class- customer service. They’ve done exactly that with their Thursday Boot Company Scout Men’s Chukka Boot ($149). The boot features suede weather safe upper. If you’re going to be running through puddles this boot would be a great option. The shaft is 4.5 inches and sits on a studded rubber sole. The studs provide extra grip on most surfaces. Additional features include two blind eyelets, stitch out construction, and a cork footbed for all-day comfort. When ordering they suggest getting a 1/2 size smaller than you wear in sneakers.

UGG Men’s Neumel Chukka Boot

I know, I know. They’re UGGs. But man, if you can get over the looks, they’re really comfortable. The UGG Men’s Neumel Chukka Boot ($130) might as well be slippers. This casual chukka is perfect for heading to the grocery store or lounging around the house. Just make sure you keep it out of the rain. The upper is made out of a hearty suede with a luxurious wool lining. No socks needed. The shaft measures just 3.75 inches which is a little shorter than other Chukkas on our list. It also features a sturdy no slip flexible molded EVA outsole. These guys go great with a basic pair of jeans and a t-shirt.

Timberland Men’s EK Brook Park Chukka Boot

The Timberland Men’s EK Brook Park Chukka Boot ($140) is another boot that can take a beating. The EK Brook features a premium leather upper that allows the boot to easily be dressed up or down. Whether you’re at work or headed to happy hour this boot works. Additional features include cotton laces, leather heel welt, and a slip resistant outsole. The outsole has a unique L7 lug pattern designed for supper traction. They also suggest sizing down by a half a size than you wear sneakers.

Dr Martens Cabrillo Mens Chukka Boot

You know what I’ve never done? Worn out a pair of Dr. Martens soles. The Dr. Martens Cabrillo Bens Chukka Boot ($80) feature the same AirWair midsole and rubber soles used in their famous boots and shoes. Basically, the soles in these Chukkas will probably outlive you. The uppers feature a distressed waxed leather for some added water resistance. The silhouette also comes with two eyelets, a leather lining, and an air-cushioned sole. Oh yeah, lets not forget the signature yellow stitched midsole.

Rockport Men’s Urban Edge Chukka

The Rockport Men’s Urban Edge Chukka ($159) is another great looking shoe. These guys come in a great chocolate color. You can easily transition from day to night with these guys. The uppers are made from high-quality leather with a mesh lining. The lining works to wick moisture away from your feet. While the padded tongue prevents bruising from the laces. The whole kit sits on a rubber sole with EVA cushioned footbed infused with Adiprene by Adidas. Adiprene tech provides shock absorbing heel cushioning for comfortable all day wear.

Alden Unlined Suede Chukka Boot in Dark Brown

Alden boots are some of the best you can buy on the planet. The Alden Unlined suede Chukka Boot in Dark Brown ($563) are no different. They feature genuine welt so the soles can easily be replaced once they’ve worn out. These are the kind of shoes that can last generation. Alden has made shoes for over a 100 years. They know what they’re doing. Additional features include a brown suede calfskin leather upper. A flex welt construction. A single flexible leather outsole. And a 360-degree Goodyear storm welt.

Johnston & Murphy Men’s Copeland Chukka Boot

The Johnston & Murphy Men’s Copeland Chukka Boot ($290) come in at about half the price of the Alen’s, but they still have a lot of great features. The uppers are full grain leather with soft sheepskin lining. The uppers sit on a genuine plantation crepe outsole, with a foam cushioned performance footbed. Johnston & Murphy have been around for over 150 years. You can easily see why with the detail in these shoes.

Wolverine Liam Chukka

Wolverine is another company than utilizes traditional shoemaking in its boots. Like the Alden boots the Wolverine Liam Chukka ($195) features a time-tested Goodyear Welt construction. This construction is durable, flexible, and allows the boot to be easily resoled. They constructed the upper from 100% leather with two-eyelets and triple needle stitching detail. For the price you get a really great shoe with some nice features.

Mezlan Men’s Adra Chukka Boot

The Mezlan family started out making saddles for generations of European aristocrats. They’ve taken that history of fine workanship and applied it to making quality footwear. The Mezlan Men’s Adra Chukka Boot ($395) has all of those qualities. The lightweight chukka features a 100% leather upper made from calfskin leather. Calfskin leather offers comfort, durability, and a long-lasting fit. The whole kit sits on a rubber sole for added traction.

Allen Edmonds Men’s Surrey Weather Proof Chukka Boot

Allen Edmonds has a long history of making great boots. Their Allen Edmonds Men’s Surrey Weather Proof Chukka Boot ($350) fits in that category nicely. This boot offers not only great styling, but solid weather proofing for a chukka that you can wear in almost any condition. The Surry chukkas are named for a region in England that averages 115 days of rain per year. This boot features a suede upper with special water-repellent technology. Never worry about ruining your suede chukkas due to a little rain again. The whole water proof kit sits on a rugged commando sole with lugs for added traction. Additional features include a three eyelet silhouette, comfort foam insole and a standard 4.5″ shaft. Made in gold ole U.S. of A.

Charles Tyrwhitt Stone suede desert boot

This is a great looking boot at a great price. The Charles Tyrwhitt Stone suede desert boot ($199) has a great silhouette. Probably one of the best looking boots in the list. The upper is made from 100% Italian suede leather and has a leather lining. The upper sits on a beautiful classic crepe sole.

Trickers Polo Men’s Chukka

Wow. This shoe is simply beautiful. The Trickers Polo Me’s Chukka (£357) is an awesome looking shoe. The Polo is a new Plain apron Chukka boot, with blind eyelets for greater refinement in Coffee Castorino suede upper and finished with a Dainite sole. This is probably going to be the next pair of boots I pick up.

Church’s Church’s Ryder Men’s Chukka Boot

The Church’s Ryder Men’s Chukka Boot ($600) is another beautiful chocolate chukka on our list. They feature a suede leather upper with two eyelets. The interior lining is also leather. The shaft measure 4.5″. The kits sits on a lightly cushioned leather footbed that sits on a durable textured synthetic outsole.