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Man's Best Friend: Chukka Boots & More

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

    Calvin Klein Franz Chukka Boot

    $130, $69.97

  • J Shoes Mason Chukka Boot

    J Shoes Mason Chukka Boot

    $218.5, $99.97

  • Florsheim Doon Chukka

    Florsheim Doon Chukka

    $120, $59.97

  • Audience Charmed Summer Boot

    Audience Charmed Summer Boot

    $255, $49.97

  • Walkover Wilfred Chukka Boot

    Walkover Wilfred Chukka Boot

    $280, $139.97

  • Kenneth Cole High Pitch Chukka

    Kenneth Cole High Pitch Chukka

    $118, $69.97

  • Audience Contrast Summer Boot

    Audience Contrast Summer Boot

    $140, $39.97

  • Audience Summer Boot

    Audience Summer Boot

    $140, $39.97

  • Sperry Top-Sider Authentic Original Neon Chukka

    Sperry Top-Sider Authentic Original Neon Chukka

    $100, $49.97

  • Sperry Top-Sider Boat Chukka

    Sperry Top-Sider Boat Chukka

    $370, $149.97

  • Ocean Minded by Crocs Roa Chukka Boot

    Ocean Minded by Crocs Roa Chukka Boot

    $94.99, $64.97

  • Billy Reid Espadrille Chukka

    Billy Reid Espadrille Chukka

    $295, $149.97

  • Generic Surplus Chukka Boot

    Generic Surplus Chukka Boot

    $95, $44.97

  • Generic Surplus Apache Chukka Boot

    Generic Surplus Apache Chukka Boot

    $75, $34.97

  • Marc New York Stanton Chukka

    Marc New York Stanton Chukka

    $128, $69.97

  • Marc New York Stanton Chukka

    Marc New York Stanton Chukka

    $128, $69.97

  • Marc New York Stanton Chukka

    Marc New York Stanton Chukka

    $128, $69.97

  • Marc New York Stanton Chukka

    Marc New York Stanton Chukka

    $128, $69.97

  • John Varvatos Dylan Binded Chukka Boot

    John Varvatos Dylan Binded Chukka Boot

    $398, $169.97

  • Vanishing Elephant Classic Dessert Boot

    Vanishing Elephant Classic Dessert Boot

    $200, $99.97

  • John Varvatos Dylan Binded Chukka Boot

    John Varvatos Dylan Binded Chukka Boot

    $398, $169.97

  • Rockport Dialed In Chukka Boot

    Rockport Dialed In Chukka Boot

    $140, $59.97

  • Rockport Charson Chukka Boot

    Rockport Charson Chukka Boot

    $140, $69.97

  • Sperry Top-Sider Exclusively for Jeffrey Sedona Camo Chukka

    Sperry Top-Sider Exclusively for Jeffrey Sedona Camo Chukka

    $200, $59.97

  • Sperry Top-Sider Boat Chukka

    Sperry Top-Sider Boat Chukka

    $375, $149.97

  • A.Testoni Beatles Boot

    A.Testoni Beatles Boot

    $1225, $449.97

  • J Shoes Bailer Boot

    J Shoes Bailer Boot

    $276, $129.97

  • Reebok Exofit Clean RW Boot

    Reebok Exofit Clean RW Boot

    $159.99, $87.97

  • Reebok Classic RW Boot

    Reebok Classic RW Boot

    $154.99, $85.97

  • Reebok Classic RW Boot

    Reebok Classic RW Boot

    $154.99, $85.97

  • Dr. Martens Felipe Wingtip Lace-Up Boot

    Dr. Martens Felipe Wingtip Lace-Up Boot

    $280, $129.97

  • Dr. Martens Halen Lace-Up Zip Boot

    Dr. Martens Halen Lace-Up Zip Boot

    $300, $129.97

  • Dr. Martens Beckett Camo Lace-Up Boot

    Dr. Martens Beckett Camo Lace-Up Boot

    $200, $129.97

  • Cole Haan Stanton Chelsea Boot

    Cole Haan Stanton Chelsea Boot

    $248, $169.97

  • Rockport Dalari Wingtip Boot

    Rockport Dalari Wingtip Boot

    $135, $59.97

  • Rockport Castleton Boot

    Rockport Castleton Boot

    $160, $74.97

  • Superdry Xpedition Hiker Boot

    Superdry Xpedition Hiker Boot

    $280, $59.97

: Men

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