8 of the Best Chukka Boots for Men

When it comes to footwear, the are few forms more stylish and classy than that of the Chukka Boot and for anyone looking to add this to their repertoire this spring, you’re in luck because the guys at Huckberry have a stellar line up to choose from.

Chukka Boots look great for occasions both formal and causal and there are some great brands crafting this type of footwear so you’ve certainly got no shortage of options. Check out our pick of 8 of the best Chukka Boots for men below:

Rhodes Dylan Chukka Boots – $98

The best men’s chukka boots on the market were typically born out of necessity, with military men needing something with protection that would also be both lightweight and more breathable than the standard trench boot. These Rhodes Dylan Chukka Boots ($98) are their take on this classic and kicks things off with a supple, unlined Italian leather over a natural crepe rubber sole.

This top notch combination delivers the look of the original with unbeatable breathability. The boast the craftsmanship of a bespoke Milanese shoe and the sort of comfort which is utterly off the charts. They’re great for casual offices and warm days regardless of season, with relaxed wear extending through the weekend. ($98)


Shoe The Bear Dalton Suede Chukka Boots – $180

Offering a classic chukka boot silhouette, updated and upgraded for any occasion, it’s easy to see why these Shoe The Bear Dalton Suede Chukka Boots ($180) are one of our favourites here at Coolector HQ. Each pair is crafted from high quality suede leather that’s structured for a striking aesthetic and soft feel right out of the box. Handmade in Portugal, the smooth, rounding lines, sophisticated leather trimming, and a balanced construction allow you to confidently wear these awesome chukkas anytime, anyplace. ($180)


Astorflex Greenflex Chukka Boots – $165

This eco-friendly Desert boot, which is handmade in Italy and available exclusively at Huckberry, has definitely caught our eye here at The Coolector. The Astorflex Greenflex Chukka Boots ($165) has an aesthetic favoured by WWII desert soldiers and icons like Steve McQueen so they will add a touch of class to any outfit choices you make over the next few months. They boast an environmentally responsible construction and the 100% natural rubber soles feel like walking on a cloud. These cracking Chukkas from Astorflex are made from soft, supple nubuck leather from Europe that ages beautifully. ($165)


Lems Boulder Chukka Boots – $120

With a ridiculously comfortable suede upper, you’ll not find footwear more pleasing than these excellent Lems Boulder Chukka Boots ($120). Each pair comes with a removable, moisture-wicking PU insole and a clever rollable and packable construction which can effortlessly fit in any backpack, carry on, or luggage. The LemsRubber air-injected rubber outsole allows the shoes to be lightweight, flexible, and supremely packable while adding plenty of traction for walking on different terrains. The zero-drop design assists in the support of your spine and the wide toe box allows your toes to splay out in their natural way. ($120)


Olukai Kalia Puki Chukka Boots – $165

These excellent looking Olukai Kalia Puki Chukka Boots ($165) are made from a soft, tumbled nubuck leather with full-grain leather accents around the collar and eyelets that delivers a really eye-catching visual impact that we’re loving here at Coolector HQ. Each pair is lined with a soft leather top collar and tongue and a soft microfibre suede and a built-in mudguard helps protect the shoes. The dual-density PU footbed with gel insert and a soft microfibre footbed delivers a comfortable wear all day long and the treaded rubber outsole offers excellent traction. ($165)


Nisolo Emilio Chukka Boots – $135

This exclusive waxed leather rendition available only at Huckberry and the Nisolo Emilio Chukka Boots ($135) have a full-length, soft sheep leather insole feels great against the feet and ankle. They have built-in arch support provides all day comfort and there is an added layer of stitching between upper and leather sole for a slightly more rustic look – something that we’re big fans of here at Coolector HQ. These great looking Chukka Boots from Nisolo are handmade in Peru with a cushioned, microporous interior softens the impact when walking. ($135)


Red Wing Heritage Weekender Chukka Boots – $230

Made from full-grain oil-tanned leather from S.B. Foot Tanning leather, a Red Wing owned-and-operated tanning company based in Red Wing, Minnesota, these Chukkas are a cut above in the style and craftsmanship department. The Red Wing Heritage Weekender Chukka Boots ($230) have a stitchdown construction which allows for resoling when necessary, which extends the life of the boots. They have a comfortForce® footbed for a relaxed ride and all-day comfort and use water, stain and perspiration resistant premium leather in their crafting which delivers exceptional performance whatever the weather or terrain you face. ($230)


Vivobarefoot Gobi II Chukka Boots – $170

These lightweight, minimalist boots have an ultra-thin sole to let your feet move like feet which ensures a comfort level that is unparalleled. The Vivobarefoot Gobi II Chukka Boots ($170) are handcrafted from African leather sourced from free roaming cows and tanned by Pittards Tannery. The foam insole with cork top layer delivers impeccable insulation from the ground, but is removable for a lighter-weight and more natural ride day in, day out. These boots fold or rolls up small enough to fit inside a travel bag and the ultra-thin TPU sole offers maximum sensory feedback and encourages your foot’s natural movement. ($170)

Leo is the owner of The Coolector and writes about the stuff he loves. And some stuff that he merely likes.