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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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Frank Wright Men’s Smith Chukka Boot$140.0$59.0 -
Gorilla USA Men’s Chukka Boot$450.0$179.0 -
Robert Wayne Men’s Roma Chukka$120.0$60.0 -
John Varvatos Men’s Star S Eva Chukka$228.0$109.0 -
John Varvatos Men’s Star S Eva Chukka$228.0$109.0 -
Original Penguin Men’s Birdie Lite Chukka$140.0$65.0 -
John Varvatos Men’s Star Casual Chukka$228.0$109.0 -
Rogue Men’s Bud Chukka Boot$295.0$109.0 -
Andrew Marc Men’s Dorchester Chukka Boot$178.0$89.0 -
Andrew Marc Men’s Dorchester Chukka Boot$178.0$89.0 -
Donald J Pliner Men’s Brady Chukka Boot$375.0$175.0 -
Donald J Pliner Men’s Brady-80 Chukka Boot$375.0$175.0 -
Donald J Pliner Men’s Brady-80 Chukka Boot$375.0$175.0 -
French Connection Men’s Corian Chukka Boot$158.0$75.0 -
Gorilla USA Men’s Chukka Boot$450.0$169.0 -
Gorilla USA Men’s Chukka Boot$450.0$189.0 -
Gorilla USA Men’s Chukka Boot$450.0$179.0 -
French Connection Men’s Corian Chukka Boot$158.0$75.0 -
Tod’s Men’s Dress Chukka Boot$595.0$375.0 -
J. Artola Men’s Chuck Chukka$225.0$105.0 -
J. Artola Men’s Chuck Chukka$225.0$105.0 -
J. Artola Men’s Chuck Chukka$225.0$105.0 -
Steve Madden Men’s Garisonn Chukka Boot$115.0$59.0 -
Steve Madden Men’s Garisonn Chukka Boot$115.0$59.0 -
Jose Real Men’s Amsterdam Chukka Boot With Brogue Detail$398.0$189.0 -
Andrew Marc Men’s Dorchester Chukka$178.0$41.0 -
Joe’s Men’s Slick Chukka Boot$175.0$85.0 -
Joe’s Men’s Slick Chukka Boot$175.0$85.0 -
Steve Madden Men’s Halloway Canvas & Leather Chukka$90.0$39.0 -
Andrew Marc Men’s Dorchester Chukka$178.0$41.0 -
Tod’s Men’s Dress Chukka Boot$580.0$375.0 -
Quiksilver Men’s Marquez Low Chukka Boot$110.0$52.0 -
John Varvatos Men’s Hipster Chukka Boot$198.0$95.0 -
John Varvatos Men’s Star Classic Chukka$248.0$105.0 -
John Varvatos Men’s Star B Chukka$248.0$125.0 -
Timberland Men’s Chukka Midrise Boot$185.0$93.0 -
Frank Wright Men’s Totton Suede Chukka Boot$120.0$55.0 -
Von Dutch Men’s Toolbox Chukka Boot$155.0$75.0 -
Von Dutch Men’s Toolbox Chukka Boot$155.0$75.0 -
Von Dutch Men’s Toolbox2 Chukka Boot$144.0$65.0 -
Frank Wright Men’s Totton Suede Chukka Boot$120.0$55.0 -
Robert Wayne Men’s Double Gore Chukka$120.0$49.0 -
Andrew Marc Men’s Howard Chukka Boot$148.0$56.0 -
Frank Wright Men’s Totton Suede Chukka Boot$120.0$55.0 -
Frank Wright Men’s Totton II Chukka Boot$130.0$59.0 -
Robert Graham Men’s Bedford Casual Cap Toe Chukka$328.0$155.0 -
Timberland Men’s Brasstown Chukka$110.0$49.0 -
Bacco Bucci Men’s Vialli Suede Chukka Boot$265.0$125.0 -
Rockport Men’s Ledge Hill Too Chukka Boot$150.0$59.0 -
Pointer Footwear Men’s Surfer Rosa Mid Chukka Boot$140.0$59.0 -
Vlado Men’s Valentino-Mid Chukka Sneaker$130.0$58.0 -
Andrew Marc Men’s Parkchester Chukka Boot$178.0$55.0 -
Steve Madden Men’s Harsen Leather Chukka$90.0$39.0
