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 and edgier looks with contrast paneling—and enjoy the upgrade.
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Antonio Maurizi Men’s Chukka Boot$215.0$330.0 -
Antonio Maurizi Men’s Chukka Boot$110.0$330.0 -
Eastland Men’s Norwich 1955 Chukka Boot$110.0$86.0 -
Calvin Klein Men’s Flynn Chukka Boot$140.0$59.0 -
Calvin Klein Men’s Flynn Chukka Boot$140.0$59.0 -
Calvin Klein Men’s Flynn Chukka Boot$695.0$50.0 -
Calvin Klein Men’s Flynn Chukka Boot$500.0$50.0 -
Tommy Hilfiger Men’s Concord Chukka$500.0$65.0 -
Tommy Hilfiger Men’s Concord Chukka$500.0$65.0 -
Andrew Marc Men’s Hudson Chukka$415.0$122.0 -
Salvatore Ferragamo Men’s Palestro Chukka$425.0$528.0 -
Dino Bigioni Men’s Moc Croc Desert Boot$92.0$234.0 -
Dino Bigioni Men’s Suede Desert Boot$92.0$225.0 -
Dino Bigioni Men’s Suede Desert Boot$595.0$225.0 -
Dogen Men’s Nordve Chukka Boot$178.0$198.0 -
Bruno Magli Men’s Malcolm Chukka 2-Eyelet Laced Boot$110.0$189.0 -
Generic Surplus Men’s McNairy Chukka$150.0$36.0 -
Generic Surplus Men’s McNairy Chukka$178.0$36.0 -
Salvatore Ferragamo Men’s Pioneer Chukka Boot$125.0$452.0 -
SeaVees Men’s 12/67 3 Eye Chukka$178.0$80.0 -
Robert Wayne Men’s Lazo Chukka$150.0$66.0 -
Oliberte Men’s Dubano Short Chukka Boot$170.0$66.0 -
SeaVees Men’s 12/67 3 Eye Chukka$148.0$80.0 -
Generic Surplus Men’s Dom Mixed Material Chukka Boot$148.0$55.0 -
Andrew Marc Men’s Dorchester Chukka$148.0$89.0 -
Oliberte Men’s Dubano Short Chukka Boot$150.0$66.0 -
Rockport Men’s Eastern Empire Plain Toe Chukka Boot$295.0$83.0 -
Andrew Marc Men’s Lexington Dress Chukka Boot$425.0$80.0 -
Andrew Marc Men’s Cooper Gore Chukka$516.0$74.0 -
Andrew Marc Men’s Cooper Gore Chukka$175.0$74.0 -
Oliberte Men’s Dubano Short Chukka Boot$175.0$66.0 -
Rogue Men’s Kieth Chukka Boot$90.0$99.0 -
Bruno Magli Men’s Malcolm Chukka 2-Eyelet Laced Boot$240.0$189.0 -
testoni BASIC Men’s Chukka Boot$240.0$103.0 -
Joseph Abboud Men’s Clint Chukka Boot$128.0$79.0 -
Joseph Abboud Men’s Clint Chukka Boot$115.0$79.0 -
Tommy Hilfiger Men’s Keene Chukka Sneaker$60.0$45.0 -
Donald J Pliner Men’s Bishop Chukka$80.0$130.0 -
Donald J Pliner Men’s Bishop Chukka$119.0$130.0 -
Andrew Marc Men’s Stanton Chukka$189.0$64.0 -
Steve Madden Men’s Hillside Chukka$60.0$65.0 -
Tommy Hilfiger Men’s Roberto Chukka$80.0$21.0 -
Lugz Men’s Grant Chukka$60.0$42.0 -
Tommy Hilfiger Men’s H-STETSEN Chukka$185.0$48.0 -
Moods of Norway Men’s Moelv Chukka$175.0$87.0 -
Lugz Men’s Pathway Chukka$425.0$34.0 -
Lugz Men’s Grant Chukka$125.0$42.0 -
Lugz Men’s Pathway Chukka$198.0$29.0 -
Sebago Men’s Halyard Chukka Boot$119.0$65.0 -
Joseph Abboud Men’s John Chukka Boot$125.0$79.0 -
Tod’s Men’s Chukka Sneaker$125.0$305.0 -
Joseph Abboud Men’s Winston Chukka Boot$119.0$60.0 -
John Varvatos Men’s Hipster Work Chukka$115.0$99.0 -
Tommy Hilfiger Men’s Chukka Boot$185.0$68.0 -
Joseph Abboud Men’s Eastwood Chukka Boot$75.0$60.0 -
Joseph Abboud Men’s Eastwood Chukka Boot$160.0$60.0 -
Tommy Hilfiger Men’s Chukka Boot$140.0$68.0 -
Steve Madden Men’s Hillside Chukka Casual Boot$198.0$65.0 -
Sebago Men’s Halyard Chukka Boot$90.0$65.0 -
Burnetie Men’s Mid Mark Chukka Sneaker$$39.0 -
Sorel Men’s Balmoral Halfcab Chukka Boot$$56.0 -
Rockport Men’s Charson Lace-Up Boot$$39.0 -
John Varvatos Men’s Redding Chukka$$39.0 -
Robert Wayne Men’s Ostia Wing Tip Chukka Boot$$17.0