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These mid-top marvels deliver sneaker-caliber comfort, but with a more polished vibe. Chukka boots manage to fit in to happy hour, date night and weekend looks, while standing out in a sea of tired kicks. Choose from polished, sueded, moc-toe and more—and enjoy the upgrade.
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John Varvatos Men’s Redding Chukka (Dark Brown)$198.0$85.0 -
The Generic Man Men’s Florentine Chukka (Natural)$340.0$109.0 -
The Generic Man Men’s Florentine Chukka (Baby Blue)$340.0$109.0 -
Florsheim by Duckie Brown Men’s Military Chukka Boot (Camel Suede)$475.0$239.0 -
Calvin Klein Men’s Franz Chukka Boot (Navy)$130.0$65.0 -
Calvin Klein Men’s Franz Chukka Boot (Grey)$130.0$65.0 -
Calvin Klein Men’s Franz Chukka Boot (Dark Tan)$130.0$65.0 -
Tod’s Men’s Chukka Boot (Grey)$575.0$408.0 -
John Varvatos Men’s Redding Chukka (Black)$198.0$85.0 -
The Generic Man Men’s Riderman Chukka (Mustard)$430.0$88.0 -
John Varvatos Men’s Redding Chukka (Royal Blue)$198.0$85.0 -
John Varvatos Men’s Redding Chukka (Stone)$198.0$85.0 -
Ben Sherman Men’s Sinclair Boot (Natural Canvas/Tan Leather)$115.0$79.0 -
Ben Sherman Men’s Sinclair Boot (Navy Canvas/Tan Leather)$115.0$79.0 -
Andrew Marc Men’s Dorchester Saddle Chukka Boot (Avion/White/Cymbal)$178.0$89.0 -
Andrew Marc Men’s Dorchester Saddle Chukka Boot (Black/White/Cymbal)$178.0$89.0 -
Andrew Marc Men’s Parkchester Chukka Boot (Stone/White/Natural)$178.0$89.0 -
Oliberte Men’s Zimbo Boot (Tan)$170.0$89.0 -
Oliberte Men’s Zimbo Boot (Brown Yellow)$170.0$89.0 -
Andrew Marc Men’s Parkchester Chukka Boot (Avion/White/Natural)$178.0$89.0 -
John Varvatos Men’s Hipster Chukka (Nickel)$198.0$89.0 -
Tod’s Men’s Chukka Boot (Brown)$545.0$387.0 -
MARC NEW YORK Men’s Eldridge Chukka Boot (Brown/Khaki Cream)$78.0$52.0 -
Rogue Men’s Drakon Plain Toe Bootie (Navy)$198.0$99.0 -
Rogue Men’s Drakon Plain Toe Bootie (Light Grey)$198.0$99.0 -
Rogue Men’s 3-Eye Chukka Boot (Light Grey)$195.0$99.0 -
Rogue Men’s 3-Eye Chukka Boot (Beige)$195.0$99.0 -
Florsheim Men’s Highlands Chukka Boot (Gray/Black)$135.0$49.0 -
Generic Surplus Men’s McNairy Chukka Sneaker (Military)$79.0$25.0 -
Generic Surplus Men’s McNairy Chukka Sneaker (Natural)$79.0$25.0 -
Tod’s Men’s Chukka Boot (Blue)$535.0$269.0 -
Tod’s Men’s Chukka Boot (Black)$435.0$305.0 -
Tod’s Men’s Chukka Boot (Light Brown)$495.0$347.0 -
Tod’s Men’s Chukka Boot (Brown)$530.0$235.0
