A crafty combination of casual cool meets urban sophistication, the chukka boot has solidified itself as a guy’s footwear essential. Multi-tasking and season-spanning, this simple silhouette is quickly becoming man’s best friend—a go-to finishing for dressed up and down looks. Slipped on or laced up, each pair promises a polished but laidback sensability.
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Calvin Klein Franz Chukka Boot
$130, $69.97 -
J Shoes Mason Chukka Boot
$218.5, $99.97 -
Florsheim Doon Chukka
$120, $59.97 -
Audience Charmed Summer Boot
$255, $49.97 -
Walkover Wilfred Chukka Boot
$280, $139.97 -
Kenneth Cole High Pitch Chukka
$118, $69.97 -
Audience Contrast Summer Boot
$140, $39.97 -
Audience Summer Boot
$140, $39.97 -
Sperry Top-Sider Authentic Original Neon Chukka
$100, $49.97 -
Sperry Top-Sider Boat Chukka
$370, $149.97 -
Ocean Minded by Crocs Roa Chukka Boot
$94.99, $64.97 -
Billy Reid Espadrille Chukka
$295, $149.97 -
Generic Surplus Chukka Boot
$95, $44.97 -
Generic Surplus Apache Chukka Boot
$75, $34.97 -
Marc New York Stanton Chukka
$128, $69.97 -
Marc New York Stanton Chukka
$128, $69.97 -
Marc New York Stanton Chukka
$128, $69.97 -
Marc New York Stanton Chukka
$128, $69.97 -
John Varvatos Dylan Binded Chukka Boot
$398, $169.97 -
Vanishing Elephant Classic Dessert Boot
$200, $99.97 -
John Varvatos Dylan Binded Chukka Boot
$398, $169.97 -
Rockport Dialed In Chukka Boot
$140, $59.97 -
Rockport Charson Chukka Boot
$140, $69.97 -
Sperry Top-Sider Exclusively for Jeffrey Sedona Camo Chukka
$200, $59.97 -
Sperry Top-Sider Boat Chukka
$375, $149.97 -
A.Testoni Beatles Boot
$1225, $449.97 -
J Shoes Bailer Boot
$276, $129.97 -
Reebok Exofit Clean RW Boot
$159.99, $87.97 -
Reebok Classic RW Boot
$154.99, $85.97 -
Reebok Classic RW Boot
$154.99, $85.97 -
Dr. Martens Felipe Wingtip Lace-Up Boot
$280, $129.97 -
Dr. Martens Halen Lace-Up Zip Boot
$300, $129.97 -
Dr. Martens Beckett Camo Lace-Up Boot
$200, $129.97 -
Cole Haan Stanton Chelsea Boot
$248, $169.97 -
Rockport Dalari Wingtip Boot
$135, $59.97 -
Rockport Castleton Boot
$160, $74.97 -
Superdry Xpedition Hiker Boot
$280, $59.97
