10 Best Chukka Boots of December 2025

• The finish or polish on these boots show marks which are not scratches
• Chukka boot silhouette , Two eyelet lace-up front , Cushioned insole
• Upper material - suede. Lining material-leather
• Note:Color shade may vary due to lighting

Clarks

• Classic STYLE: we have your style needs covered with great street and trail Ready performance. Our well styled assortment of rugged men’s casual shoes is designed to fit in with your casual and outdoor ready ensembles wherever you go!
• Comfort: Nunn Bush created one of the most comfortable and breathable rugged casual shoes for men you can find! Designed with comfort gel and memory foam insole to cushion your every step
• Perfect FIT: pamper your feet with this amazing rugged casual walking shoe that is constructed with premium materials to provide the highest level of fit integrity. Available in Medium width and wide Widths for the perfect fit
• Outsole: Lightweight rubber sole with rugged lug tread for extra traction and superior shock absorption
• Value: Nunn Bush is highly regarded as a premier footwear brand by providing the best value and style in fine Men's footwear since 1912

Nunn Bush

• Mid-cut boot in waterproof leather with waxed flat laces and plush collar
• Comfort system designed to provide lightweight shock absorption.
• Hydro-shield construction with waterproof leather, seam sealing, waterproof insole board, and non-wicking laces
• Thermoplastic slip-resistant outsole

Rockport

• Leather
• Tons of Doc's DNA, like grooved edges, logo heel tab and yellow welt stitching
• Built on the iconic AirWair air-cushioned sole
• The Dr. Martens Cabrillo offers a perfect broken-in look, making it ideal for everyday wear.

Dr. Martens

• Soft suede upper
• Treadlite by UGG outsole for comfort and durability
• EVA insole with textile lining

UGG

• Chukka boot featuring blind-eyelet lacing and slightly distressed finish. Textile lining

Steve Madden

• Relax fit
• Memory foam

Skechers

• Heel Height .98 inches
• Boot Dimensions: shaft Width 4.13 inches, Shaft Circumference 9.84 inches, Shaft height 3.93 inches
• Comfort Features: Removable Ortholite footbed, Rubber midsole, flexible EVA outsole, Smooth Textile Linings, arch and Heel Support
• Premium leather and suede

Clarks

• Slightly padded insole
• Pop of color with a brick colored sole

Unlisted by Kenneth Cole

• Mocc-toe chukka boot featuring perforated side panels and lace-up front with metal eyelets
• Padded tongue and collar
• Rear pull loop
• Gel-infused memory foam cushioned insole
• Shock-absorbing supportive midsole
• Flexible rubber high-traction outsole

Skechers