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There comes a time in every guy’s life when it’s time to swap those beloved sneakers for something a bit more stylized. Fret not. These chukkas are just as comfortable as your dependable kicks, yet they give the jeans and T-shirt formula a much-needed injection of sophistication. Pair any of these styles with cuffed chinos and a flannel button-down for a foolproof weekend look.
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Stacy Adams Men’s Taliesin Chukka (Black Suede)$85$51.00 -
Calvin Klein Men’s Ference Chukka (Black)$130$65.00 -
John Varvatos Star USA Men’s Sid Commuter Chukka (Coal)$178$115.00 -
Bed|Stü Men’s Uncle Dowell Chukka (Black)$85$45.00 -
John Varvatos Men’s Hipster Chukka (Lead)$550$275.00 -
Tretorn Men’s Obo GTX Leather Chukka (Black/gum)$180$79.00 -
Tretorn Men’s Obo GTX Leather Chukka (Brown)$180$79.00 -
J SHOES Men’s Sonar Leather Shoe with Ties (Chocolate)$150$75.00 -
Sebago Men’s Beacon Chukka (Brown)$130$75.00 -
Sebago Men’s Beacon Chukka (Brown Oiled Waxy)$130$75.00 -
Bed|Stü Men’s Lucious Chukka Boot (Brown)$598$79.00 -
Bed|Stü Men’s Lucious Chukka Boot (Brown Pebble)$120$79.00 -
John Varvatos Men’s Hipster Chukka (Espresso)$195$299.00 -
Tommy Hilfiger Men’s Lark Chukka Boot (Dark Brown)$140$59.00 -
H by Hudson Men’s Aura Chukka Sneaker (Mustard)$195$99.00 -
Ben Sherman Men’s Aberdeen Woven Chukka (Brown)$135$69.00 -
H by Hudson Men’s Aura Chukka Sneaker (Taupe)$165$99.00 -
Wolverine No. 1883 Men’s Orville Shoe (Milkshake)$80$69.00 -
WeSC Men’s Lawrence Chukka (Oatmeal)$215$89.00 -
Stacy Adams Men’s Dynamo Chukka (Brick)$140$48.00 -
J. Artola Men’s Brandon MX Chukka (Dark Brown)$108$89.00 -
Geox Men’s Juan Chukka (Beige)$140$49.00 -
Kenneth Cole Reaction Men’s Drift Racing Chukka (Grey)$100$54.00 -
Ben Sherman Men’s Abner Chukka (Dark Brown)$100$63.00 -
Cushe Men’s Bespoke Chukka Boot (Brown)$165$49.00 -
Cushe Men’s Bespoke Chukka Boot (Grey)$465$49.00 -
WeSC Men’s Lawrence Chukka (Beluga)$90$89.00 -
Tod’s Men’s Chukka (Ivory)$110$232.00 -
Tretorn Men’s Oken Chukka (Gunmetal)$$39.00 -
Tretorn Men’s Kasper 2.0 Suede Chukka (Gunmetal)$$49.00
