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A go-to style for the season, the chukka boot is right with almost everything in your fall wardrobe. Pair these comfortable shoes with your wear-to-work basics for a quirky touch or with your casual pieces for a refined yet relaxed look. They’re a staple in a modern guy’s cool-weather wardrobe.
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Brunello Cucinelli Men’s Casual Chukka Boot$1140.0$535.0 -
Brunello Cucinelli Men’s Casual Chukka Boot$1140.0$535.0 -
Woolrich Men’s Lane Casual Chukka Boot$160.0$65.0 -
Gorilla USA Men’s Chukka Boot$450.0$162.0 -
Robert Wayne Men’s Roma Chukka$120.0$55.0 -
Original Penguin Men’s Birdie Lite Chukka$140.0$65.0 -
John Varvatos Men’s Star S Eva Chukka$228.0$109.0 -
John Varvatos Men’s Star S Eva Chukka$228.0$109.0 -
John Varvatos Men’s Star Casual Chukka$228.0$109.0 -
Donald J Pliner Men’s Brady Chukka Boot$375.0$175.0 -
Mezlan Men’s Dress Chukka Boot$425.0$215.0 -
Mezlan Men’s Dress Chukka Boot$425.0$215.0 -
Frank Wright Men’s Smith Chukka Boot$140.0$53.0 -
French Connection Men’s Corian Chukka Boot$158.0$69.0 -
Ecco Men’s Turn Chukka$230.0$128.0 -
Gorilla USA Men’s Chukka Boot$450.0$162.0 -
Andrew Marc Men’s Dorchester Chukka Boot$178.0$80.0 -
Andrew Marc Men’s Dorchester Chukka Boot$178.0$80.0 -
Donald J Pliner Men’s Brady-80 Chukka Boot$375.0$141.0 -
Donald J Pliner Men’s Brady-80 Chukka Boot$375.0$141.0 -
Gorilla Men’s Landon Quilted Chukka Sneaker$75.0$29.0 -
Gorilla Men’s Landon Quilted Chukka Sneaker$75.0$29.0 -
Gorilla Men’s Landon Quilted Chukka Sneaker$75.0$29.0 -
Andrew Marc Men’s Stanton Chukka Boot$128.0$59.0 -
Gorilla USA Men’s Chukka Boot$450.0$162.0 -
Rick Owens Men’s Casual Chukka$1680.0$675.0 -
Rick Owens Men’s Casual Chukka$1680.0$675.0 -
J. Artola Men’s Chuck Chukka$225.0$100.0 -
J. Artola Men’s Chuck Chukka$225.0$100.0 -
J. Artola Men’s Chuck Chukka$225.0$100.0 -
Andrew Marc Men’s Kane Chukka Boot$148.0$69.0 -
Tod’s Men’s Dress Chukka Boot$595.0$345.0 -
French Connection Men’s Corian Chukka Boot$158.0$69.0 -
Andrew Marc Men’s Kane Chukka Boot$148.0$69.0 -
Lugz Men’s Grant Chukka Boot$80.0$39.0 -
Brunello Cucinelli Men’s Casual Chukka Boot$845.0$389.0 -
Andrew Marc Men’s Stanton Chukka Boot$128.0$59.0 -
Rogue Men’s Drave Casual Chukka$225.0$89.0 -
Andrew Marc Men’s Stanton Chukka Boot$128.0$59.0 -
Kenneth Cole Reaction Men’s Off The Books Chukka Sneaker$98.0$38.0 -
Kenneth Cole Reaction Men’s Off The Books Chukka Sneaker$98.0$38.0 -
Joe’s Men’s Slick Chukka Boot$175.0$77.0 -
Joe’s Men’s Slick Chukka Boot$175.0$77.0 -
John Varvatos Men’s Star Classic Chukka$248.0$98.0 -
French Connection Men’s Falon Chukka Sneaker$138.0$65.0 -
Tod’s Men’s Dress Chukka Boot$580.0$346.0 -
Wesc Men’s Chukka Boot$158.0$75.0 -
Wesc Men’s Chukka Boot$158.0$75.0 -
Timberland Men’s Chukka Midrise Boot$185.0$93.0 -
Woolrich Men’s Lane Casual Chukka Boot$160.0$59.0 -
Steve Madden Men’s Garisonn Chukka Boot$115.0$59.0 -
John Varvatos Men’s Star B Chukka$248.0$112.0 -
Von Dutch Men’s Toolbox Chukka Boot$155.0$69.0 -
Ben Sherman Men’s Otis Chukka Sneaker$150.0$35.0 -
Ben Sherman Men’s Otis Chukka Sneaker$150.0$35.0 -
Maians Men’s Marcial Ante Chukka Sneaker$150.0$67.0 -
Maians Men’s Marcial Ante Chukka Sneaker$150.0$67.0 -
Maians Men’s Marcial Ante Chukka Sneaker$144.0$67.0 -
Maians Men’s Marcial Ante Chukka Sneaker$120.0$67.0 -
Von Dutch Men’s Toolbox2 Chukka Boot$90.0$58.0 -
Frank Wright Men’s Totton Suede Chukka Boot$110.0$47.0 -
Ben Sherman Men’s Victor Chukka Sneaker$120.0$45.0 -
Quiksilver Men’s Marquez Low Chukka Boot$88.0$44.0 -
Frank Wright Men’s Totton Suede Chukka Boot$120.0$47.0 -
Andrew Marc Men’s Wythe Chukka Sneaker$88.0$36.0 -
Frank Wright Men’s Totton Suede Chukka Boot$145.0$47.0 -
Andrew Marc Men’s Wythe Chukka Sneaker$85.0$62.0 -
Von Dutch Men’s Screwdriver Chukka Sneaker$130.0$62.0 -
Ben Sherman Men’s Victor Chukka Sneaker$80.0$39.0 -
Frank Wright Men’s Totton II Chukka Boot$120.0$56.0 -
Lugz Men’s Grant Chukka Boot$90.0$40.0 -
Robert Wayne Men’s Double Gore Chukka$160.0$44.0 -
Union Bay Men’s Wallingford Chukka Boot$$35.0 -
Woolrich Men’s Lane Casual Chukka Boot$$65.0
