Men's Chukka Boots (28)

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Head out for a casual day wearing the
Head out for a casual day wearing the Cole Haan Morris Chelsea Boots. These ankle boots feature a leather and textile-covered molded footbed that offers comfort and flexibility. The rubber outsole with an authentic texture provides extra flexibility and traction. ...
Finish your cool looks with a touch of
Finish your cool looks with a touch of classic when you add the Copeland Chelsea boots from Johnston & Murphy into the mix. Full grain leather uppers Soft sheepskin and moisture-wicking textile linings Cushioned, memory-foam insole with sheepskin and performance-mesh ...
A handsome pull-on boot by Vance Co. This
A handsome pull-on boot by Vance Co. This Chelsea styled silhouette features flexible stretch goring on either side and a pull tab, keeping it true to its roots. The Garrett is finished with a cap-toe and brogue detailing that adds ...
Born in Milwaukee, the Nunn Bush Barklay Plain
Born in Milwaukee, the Nunn Bush Barklay Plain Toe Chukka Boots feature a modern profile, textured suede or crazy horse leather upper, and a two-tone sole. True to its hardworking Midwest roots, these shoes are a stand out for their ...
Alpha by Territory are all-time favorite Chukka boots
Alpha by Territory are all-time favorite Chukka boots featuring a heavy-duty outsole and made from genuine leather. This ankle boot style creates a versatile look from casual to dressy with a change of pants. The contrasting suede accents add a ...
An upgraded version of one of our most
An upgraded version of one of our most popular styles, the Titantwo. This rugged high-top boot by Territory draws inspiration from outdoor pursuits with a protective rubber capped toe, heel guard, and a durable EVA/rubber hybrid outsole. Authentic leather materials ...
A boot that takes you places, the Grant
A boot that takes you places, the Grant by Thomas & Vine. This round-toe boot is crafted with waterproof authentic leather resting on an 6 mm Tru Comfort Foam™ footbed and traction sole for extra support. A cushioned collar covered ...

Chukka Boots

Put your best foot forward with men’s chukka boots from Belk. With clean-cut styling and comfort built right in, there’s no need to choose between looking sharp and feeling great. Wear this classic men’s footwear with nearly everything in your closet. Whether you choose men’s jeans and a graphic t-shirt or go smart casual — leather or suede chukka boots are the perfect choice to round out your look.

Chukka boots are ideal for any casual day. For dressier occasions, leather chukkas in a dark color strike the right tone. Consider pairing men’s chinos with a patterned, button down shirt. Add a men’s sport coat, casual tie and a pair of leather chukka boots for a stylish look that’s both professional and comfortable. These boots are perfect for breakfast or date night.

Browse our collection of men’s chukka boots from top brands including Cole Haan, Florsheim, Frye, Johnston & Murphy, Sperry® and more. This versatile footwear takes on many looks for a variety of occasions. Nunn Bush offers dress chukka boots with hand-burnished leather uppers and fine, oxford styling — perfect for pairing with dress socks and a business suit. Other brands offer chukkas with construction and soles that work well as men’s hiking boots, rain boots or even some that look like sneakers. With so many styles to choose from, pick up a couple pairs to round out your wardrobe.