Chukka Boots were made popular in the 1940s & 50′s and, recently, they’ve made a resurgence back into the limelight of men’s fashion, and for good reason. Thanks to their ankle-length height, the style provides great support while still allowing for full maneuverability, which is particularly useful during winter months where soggy weather can make wearing lower cut shoes a disaster. Also, depending on the material, Chukkas are one of the few boots out there that exist for both dressy and casual settings. So, in the spirit of keeping you in the know, we’ve gathered together a collection of Chukka’s from a wide variety of footwear companies. We’ve considered a broad array of materials, colors, and price points, so if you’re in the market for picking up a pair this fall, save shopping time and effort by browsing through these options first.

Alden Unlined Chukka Boot

Price: $365

Sebago Arlington Chukka

Price: $130

RJ Colt Oscar Suede Chukka

Price: $110

Johnston & Murphy Gaffney Moc Chukka

Price: $185

Cole Haan Air Vance Chukka

Price: $198

Ted Baker Ashcrof

Price: $141

Eastland Seneca

Price: $90

John Varvatos Cooper Mid

Price: $249

Clarks Ecosteps Wallabee

Price: $140

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