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Updating your footwear collection for fall? Consider the chukka boot. 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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Antonio Maurizi Men’s Chukka Boot (Cognac)$725.0$363.0 -
Calvin Klein Men’s Lyle Chukka Sneaker (Black)$195.0$70.0 -
Calvin Klein Men’s Lyle Chukka Sneaker (Grey)$125.0$70.0 -
Eastland Men’s Buffalo 1955 Chukka Boot (Tan)$125.0$98.0 -
Eastland Men’s Gotham Chukka Boot (Tan Suede)$95.0$63.0 -
Eastland Men’s Gotham Chukka Boot (Brown)$95.0$63.0 -
Eastland Men’s Seneca Moc Toe Mid Boot (Tan)$198.0$50.0 -
Eastland Men’s Seneca Moc Toe Mid Boot (Bomber Brown)$340.0$50.0 -
John Varvatos Men’s Redding Chukka (Dark Brown)$340.0$85.0 -
The Generic Man Men’s Florentine Chukka (Baby Blue)$575.0$85.0 -
The Generic Man Men’s Florentine Chukka (Natural)$475.0$85.0 -
Tod’s Men’s Chukka Boot (Grey)$435.0$408.0 -
Florsheim by Duckie Brown Men’s Military Chukka Boot (Camel Suede)$435.0$239.0 -
Modern Fiction Men’s Midtop Sneaker (Dark Brown)$130.0$218.0 -
Modern Fiction Men’s Midtop Sneaker (Grey)$130.0$218.0 -
Calvin Klein Men’s Franz Chukka Boot (Navy)$130.0$65.0 -
Calvin Klein Men’s Franz Chukka Boot (Dark Tan)$198.0$65.0 -
Calvin Klein Men’s Franz Chukka Boot (Grey)$390.0$65.0 -
John Varvatos Men’s Redding Chukka (Black)$115.0$85.0 -
Robert Wayne Men’s Roma Chukka Boot (Brown Suede)$198.0$72.0 -
Wolverine No. 1883 Men’s Latham 1000 Mile Chukka (Beige)$198.0$125.0 -
Ben Sherman Men’s Sinclair Boot (Navy Canvas/Tan Leather)$135.0$79.0 -
John Varvatos Men’s Redding Chukka (Royal Blue)$135.0$69.0 -
John Varvatos Men’s Redding Chukka (Stone)$445.0$69.0 -
Florsheim Men’s Flites Chukka Boot (Chestnut)$170.0$68.0 -
Florsheim Men’s Flites Chukka Boot (Brown Suede)$170.0$68.0 -
Tod’s Men’s Chukka Sneaker (Blue)$425.0$334.0 -
Oliberte Men’s Zimbo Boot (Tan)$450.0$89.0 -
Oliberte Men’s Zimbo Boot (Brown Yellow)$425.0$89.0 -
Swear Men’s Davis 5 Chukka (Black)$198.0$69.0 -
Swear Men’s Davis 5 Chukka (Light Grey)$198.0$69.0 -
Swear Men’s Davis 5 Chukka (Navy)$138.0$69.0 -
Tod’s Men’s Chukka Sneaker (Grey Blue)$198.0$319.0 -
Tod’s Men’s Chukka Boot (Grey)$70.0$338.0 -
Tod’s Men’s Chukka Sneaker (Grey)$55.0$319.0 -
Rogue Men’s Drakon Plain Toe Bootie (Light Grey)$55.0$99.0 -
Rogue Men’s Drakon Plain Toe Bootie (Navy)$450.0$99.0 -
SeaVees Men’s Bayside Chukka (Black/Pigskin Suede)$60.0$45.0 -
John Varvatos Men’s Hipster Chukka (Nickel)$70.0$89.0 -
Lugz Men’s Garvin Low Cut Chukka Boot with Strap (Golden Wheat/Bark/Gum)$195.0$34.0 -
Lugz Men’s Strider Linen Chukka Sneaker (Light Warm Grey/White)$195.0$29.0 -
Lugz Men’s Strider Linen Chukka Sneaker (Khaki/White)$75.0$29.0 -
Tod’s Men’s Chukka Boot (Brown)$450.0$338.0 -
IZOD Men’s Cally Chukka Boot (Khaki)$$39.0 -
Lugz Men’s Garvin Low Cut Chukka Boot with Strap (Black)$$34.0 -
Rogue Men’s 3-Eye Chukka Boot (Light Grey)$$99.0 -
Rogue Men’s 3-Eye Chukka Boot (Beige)$$99.0 -
Lugz Men’s Chukka Boot (Wheat/Gum/Tan Nubuck)$$44.0 -
Tod’s Men’s Chukka Boot (Blue)$$338.0
