The 15 Best Chukka Boots For Men
Having a dependable, reliable pair of shoes that you can reach for day-after-day can present a taxing search for the seasoned style vet or the beginning menswear aficionado alike. Some shoes — like a classic pair of sneakers — are only fit for the warmer months of spring and summer. Other — like durable winter boots — can be a bit too heavy for seasonal wear. But there’s one style that’s reliably classic and ready to stand up to everything from rugged denim and a henley to slim chinos, a blue Oxford and a navy knit tie. That would be the classic leather chukka boot.
It’s a style of ankle boot that’s not to be confused with the desert boot (which features a crepe sole), but chukka boots are every bit as wearable as any other pair of shoes in your closet. Even if you thought you had all your four-season footwear needs covered, there’s no telling how fair a dependable pair of chukka boots can take you, especially with their more casual open lacing and yet sturdy construction & dressy looks. Grab one or grab all 16 of the best men’s chukka boots below — they won’t let you down.
Allen Edmonds Williamsburg Chukka Boots
Among the best men’s chukka boots, there are certain brands that nearly go without saying. Brands like Allen Edmonds, so consistent in its delivery of certified menswear classics that we’d be remiss not to include them here. Take the pleasingly refined-yet-versatile Allen Edmonds Williamsburg Chukka Boots, featuring a sleek silhouette and an imported European calfskin leather upper, plus dressier construction. These are boots to wear with your best worsted wool suit or your favorite pair of dark blue denim.
Nisolo Emilio Chukka Boot
Nisolo says that the Emilio Chukka Boots can take you from the boardroom to the bar, and we tend to agree. The rich Steel color is unique among chukka boots out there, and that’s but one o the fine qualities that make the Emilio Chukka Boots worthy of a spot on our list of the best chukka boots for men. The other defining factors? An agreeable price (under $200), durability and sustainable construction — pair them up with a leather Nisolo tote, classic cotton chinos and an olive pocket tee for reliable weekend style.
UGG Dagman Chukka Boot
Best known for cozy slippers and boots that your girlfriend or wife might love, the UGG Dagman Boot continues to represent the brand’s stylish push into the menswear arena — and that’s something we certainly appreciate. The Dagman Boots feature a soft lamb leather lining and rich suede for the type of style that works particularly well with essentials like a grey heather tee, an olive military jacket and light khaki chinos. A combo Treadlite and rubber outsole fuses durability and comfort for maximum longevity — when did you think you’d be able to say about UGG men’s boots? Best get to shopping.
Thursday Boots Brown Scout Chukkas
Combine the looks of a premium dress boot on top — that’s thanks to the rich brown chrome leather — with the dependability of a durable rubber outsole, and you’ve got a pair of chukka boots that give you some major bang for their buck. At under $150, the Brown Scout Chukka Boot is sharp and almost effortlessly wearable year-round — it just looks that great, right down to the flat wax laces that provide some dressy appeal. The cut of this chukka boot is slightly higher on the ankle than other similar varieties, so it looks just as sharp with a tailored suit as it does with beat-up denim.
Rhodes Footwear Tyler Chukka
These Rhodes Footwear Tyler Chukka boots are made in Mexico using only the highest-quality tumbled leather, built by experienced bootmakers from the shoe industry capital of North America. Lightweight, with an extra slip-resistant polyurethane sole, the boots have just the right amount of cushioning to be supremely comfortable without sacrificing an iota of durability. The more you wear the shoe, the more the patina will develop and the sleeker the leather will look. Built to last you a lifetime.
Frye Paul Chukka
Designed for maximum chic, these Frye Paul Chukka boots are among the classiest you’ll ever own. The antique-styled Chelsea boots are easy to slip on and off thanks to the integrated pull tab and elasticated side panel, but the durable leather will keep your feet secure and stable while you saunter around town. Made with super tough rubber for the outsole, they’re the boot that will never let you down, no matter how rough you are on them.
Timberland Men’s Oakrock LT Chukka Boots
Timberland brings the badass with these Oakrock LT chukka boots. Made with full grain leather that meet “Better Leather” standards, the boots are sleek and stylish while still promising durability that will last you for years of hardcore use. They’re an eco-conscious man’s top pick, not to mention some of the most comfortable boots you’ll ever slip on. The fabric interior lining is soft as a cloud and the cushioning will provide excellent support for your feet. You’re in for a real treat with these bad boys.
Adelante Shoe Co. The Santiago
Adelante Shoe Co. delivers a truly unique style choice with The Santiago. The tough nubuck leather has a buttery feel and a one-of-a-kind finish that makes them immediately stand out from the pack. The stacked leather heel is hyper-tough and offers amazing support, and the high-density insoles keep your feet comfy all day long. These boots are handcrafted by skilled leatherworkers in Guatemala, and every pair bought funds a care package delivered to Guatemalans affected by the pandemic. Talk about giving back while still getting high quality products.
Frye William Monk Chukka
Dignified: that’s the word best used to describe the Frye William Monk Chukka boot. Made from high-quality leather in a unique style, these shoes are slim, svelte, and chic with a construction that is as tough as it is beautiful. The rubber sole delivers excellent stability and traction, making them perfect to wear even in rainy weather. The boot is beautifully easy to slip on, but with the buckle secured across your forefoot, you can walk fully confident that it’s going nowhere no matter how far you do.
Brooks Brothers 1818 Footwear Lug-Sole Leather Chukka Boots
Brooks Brothers products are known for their finesse and elegance, and the 1818 Lug-Sole Leather Chukka boots exemplify exactly that. Made in Italy by skilled craftsmen using only the finest leather and rubber, the shoe will serve as the perfect base for your classy work, formal, or semi-formal outfit. The anatomical form used to make the shoe maximizes its support and comfort, and you’ll love how solid they feel every time you slip them onto your feet.
Red Wing Chukka Boot
Bring your A-game to any event with these Red Wing Chukka boots. These US-made boots are simple yet surprisingly classy, especially when paired with the right slacks or dress pants. The classic silhouette is a style that’s timeless, good year after year, no matter how much footwear tastes change. With its sleek leather upper and its super-tough rubber sole, this is a pair of boots that you know will deliver quality and comfort for years to come.
Cole Haan Frankland Grand Waterproof Chukka Boot
Go well outside the box with Cole Haan’s Frankland Grand Waterproof Chukka boot. The leather is fully waterproof, making it perfect for use in rainy or even snowy conditions, but you’ll love how warm and snug they are. The excellent arch support is matched only by the ankle stability offered by the padded collar and integrated laces, and once you feel the energy return provided by the Ortholite heel pod, you’ll never look at another pair of boots again.
Sanders Grain Playboy Chukka Boot
It’s not exaggerating to say that there are no other shoes quite like the Sanders Grain Playboy Chukka boot. The boot is utterly unique, with delicate curves and a truly one-of-a-kind style that will pair perfectly with formal and business attire. The Italian leather can handle anything you throw at it, and the black crepe sole feels lighter than rubber without sacrificing traction. Handmade in England by skilled craftsmen, these are the ideal shoes for the fashion-forward gentleman.
Shoe The Bear Phoenix Suede Boots
Shoe the Bear is all about style and flair, and the Phoenix Suede boots deliver exactly that. The cowhide suede leather is super tough but maximizes the chic appeal, with a classic Chukka silhouette and easy slip-on design that you can’t help but love. Made in Portugal using top-quality materials, this boot will be exactly what you need for a jaunt around town or a day sipping cocktails in your favorite classy eateries.
Allen Edmonds Discovery Chukka Boots
If you’re looking for the perfect marriage between class and durability, look no further than the Allen Edmonds Discovery Chukka boots. The classic modern Chukka style gives you a flair that strikes a perfect balance between casual, comfortable, and stylish. It’s built using premium vegetable-tanned leather paired with a solid Goodyear welted sole, including natural rubber and recycled content to make the boots as sustainable as they are comfortable.
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