We may earn money or products from the companies mentioned in this post.
Meet your new favorite footwear. These boots and chukkas deliver sneaker-caliber comfort, but with a more polished vibe. They manage to fit in to happy hour, date night and weekend looks, while standing out in a sea of tired kicks. Choose from burnished, sueded, moc-toe and more—and enjoy the upgrade.
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Kenneth Cole New York Men’s Legal Jar-Gon Chelsea Boot$198.0$99.0 -
Kenneth Cole New York Men’s Legal Jar-Gon Chelsea Boot$198.0$99.0 -
Modern Vintage Men’s Kaleb Perforated Boot$375.0$185.0 -
Andrew Marc Men’s Hillcrest Lace-up Boot$248.0$99.0 -
SeaVees Men’s 12/62 Maslon Desert Boot$138.0$69.0 -
Marc NY Men’s Hudson Chukka Boot$220.0$128.0 -
7 For All Mankind Men’s Jett Lowrise Boot$220.0$125.0 -
7 For All Mankind Men’s Jett Lowrise Boot$220.0$125.0 -
7 For All Mankind Men’s Indigo Lace-Up Boot$235.0$130.0 -
7 For All Mankind Men’s Indigo Lace-Up Boot$235.0$130.0 -
Modern Vintage Men’s Adriel Chukka Boot$350.0$159.0 -
Marc NY Men’s Hudson Chukka Boot$128.0$89.0 -
7 For All Mankind Men’s Cruz Desert Boot$250.0$130.0 -
7 For All Mankind Men’s Cruz Desert Boot$250.0$130.0 -
Modern Vintage Men’s Blaine Lace-Up Boot$395.0$179.0 -
7 For All Mankind Men’s Cassius Lace-Up Boot$250.0$125.0 -
Andrew Marc Men’s Vasser Lace-Up Boot$328.0$164.0 -
Andrew Marc Men’s Bayside Lace-Up Boot$328.0$164.0 -
Andrew Marc Men’s Lexington Dress Chukka Boot$148.0$80.0 -
Tommy Hilfiger Men’s Barnet Wingtip Boot$120.0$60.0 -
Tommy Hilfiger Men’s Barnet Wingtip Boot$120.0$60.0 -
Modern Vintage Men’s Jayden Lace-Up Boot$325.0$159.0 -
Calvin Klein Men’s Flynn Chukka Boot$110.0$59.0 -
Ben Sherman Men’s Sarge Wingtip Lace-Up Boot$170.0$81.0 -
Ben Sherman Men’s Sarge Wingtip Lace-Up Boot$170.0$81.0 -
Andrew Marc Men’s Bayside Lace-Up Boot$328.0$164.0 -
Ben Sherman Men’s Miller Rugged Lace-Up Boot$185.0$84.0 -
Ben Sherman Men’s Miller Rugged Lace-Up Boot$185.0$84.0 -
Ben Sherman Men’s Troy Mixed Material Chukka$155.0$70.0 -
Rogue Men’s Gregory Short Lace-Up Boot$250.0$117.0 -
Rogue Men’s Gregory Short Lace-Up Boot$250.0$117.0 -
Moods of Norway Men’s Oppdal Boot$279.0$149.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 7 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 10 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 8 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 11 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 9 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 8.5 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 10.5 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 9.5 M$98.0$50.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 11.5 M$98.0$50.0 -
Tommy Hilfiger Men’s Concord Chukka$140.0$65.0 -
Tommy Hilfiger Men’s Concord Chukka$140.0$65.0 -
Calvin Klein Men’s Flynn Chukka Boot$110.0$66.0 -
Andrew Marc Men’s Hudson Chukka$118.0$89.0 -
Kenneth Cole New York Men’s Cross My Mind Lace-Up Boot$218.0$109.0 -
Ben Sherman Men’s Kenneth Rugged Lace-Up Boot$175.0$84.0 -
SeaVees Men’s 09/65 Bayside Lace-Up$138.0$65.0 -
Kenneth Cole New York Men’s Cross My Mind Lace-Up Boot$218.0$109.0 -
SeaVees Men’s 02/60 5 Eye Trail Short Boot$188.0$85.0 -
SeaVees Men’s 12/67 3 Eye Chukka$178.0$80.0 -
Generic Surplus Men’s Mojave Mixed Material Lace-up Boot$145.0$66.0 -
Generic Surplus Men’s Mojave Mixed Material Lace-up Boot$145.0$66.0 -
Andrew Marc Men’s Haven Desert Boot$178.0$89.0 -
Andrew Marc Men’s Haven Desert Boot$178.0$89.0 -
Andrew Marc Men’s Haven Desert Boot$178.0$89.0 -
John Varvatos Men’s Hipster Work Chukka$198.0$99.0 -
John Varvatos Men’s Hipster Work Chukka$198.0$99.0 -
Ben Sherman Men’s Century Cap Toe Brogue Boot$185.0$84.0 -
Vince Camuto Men’s Dario Side Zip Wing Tip Lace Up Bootie$150.0$69.0 -
Vince Camuto Men’s Dario Side Zip Wing Tip Lace Up Bootie$150.0$69.0 -
Bacco Bucci Men’s Balboni Wingtip Boot$275.0$149.0 -
Bacco Bucci Men’s Balboni Wingtip Boot$275.0$149.0 -
Andrew Marc Men’s Howard Desert Boot$148.0$74.0 -
Vince Camuto Men’s Carlo Side Zip Boot$150.0$69.0 -
Robert Wayne Men’s Double Gore Chukka$120.0$60.0 -
Andrew Marc Men’s Gotham Lace-up Boot$218.0$109.0 -
Joseph Abboud Men’s Liam Wingtip Chelsea Boot$175.0$79.0 -
Andrew Marc Men’s Cooper Gore Chukka$148.0$74.0 -
Andrew Marc Men’s Howard Desert Boot$148.0$74.0 -
Joseph Abboud Men’s Thomas Chukka Boot$150.0$69.0 -
Florsheim Men’s Welter Plain Boot$110.0$55.0 -
Vince Camuto Men’s Armond Chukka$125.0$60.0 -
Vince Camuto Men’s Armond Chukka$125.0$60.0 -
Rogue Men’s Glotac Mixed Material Lace-up Bootie$350.0$102.0 -
Rogue Men’s Glotac Mixed Material Lace-up Bootie$350.0$102.0 -
SeaVees Men’s 12/67 3 Eye Chukka$178.0$80.0 -
Andrew Marc Men’s Walker Lace-Up Boot$248.0$124.0 -
Andrew Marc Men’s Cooper Gore Chukka$148.0$74.0 -
Ben Sherman Men’s Ralph Cap Toe Lace-Up Boot$175.0$84.0 -
Ben Sherman Men’s Ralph Cap Toe Lace-Up Boot$175.0$84.0 -
Andrew Marc Men’s Wilson Ankle Boot$228.0$114.0 -
G.H. Bass & Co. Men’s Boot$129.0$64.0 -
G.H. Bass & Co. Men’s Boot$129.0$64.0 -
Vince Camuto Men’s Carmine Double Gore Chukka$125.0$60.0 -
Andrew Marc Men’s Standard Ankle Boot$218.0$109.0 -
Andrew Marc Men’s Dorchester Chukka$178.0$89.0 -
SeaVees Men’s 12/62 Maslon Desert Boot$138.0$69.0 -
Andrew Marc Men’s Eugene Ankle Boot$198.0$99.0 -
Generic Surplus Men’s Mojave Lace-up Boot$145.0$53.0 -
Generic Surplus Men’s Mojave Lace-up Boot$145.0$53.0 -
Kenneth Cole REACTION Men’s Tail Me Nu Short Boot$148.0$74.0 -
Andrew Marc Men’s Christopher Oxford$128.0$64.0 -
Generic Surplus Men’s Dom Mixed Material Chukka Boot$125.0$50.0 -
Joseph Abboud Men’s Philip Wingtip Lace-Up Boot$175.0$79.0 -
Andrew Marc Men’s Howard Desert Boot$148.0$74.0 -
G. H. Bass Men’s Elmwood Wingtip Boot$129.0$76.0 -
Calvin Klein Men’s Flynn Chukka Boot$110.0$50.0 -
SeaVees Men’s 09/65 Bayside Lace-Up$138.0$65.0 -
Kenneth Cole New York Men’s Change Agent Ankle Boot$198.0$99.0 -
Joseph Abboud Men’s Lewis Wingtip Lace-Up Boot$150.0$69.0 -
Joseph Abboud Men’s Thomas Chukka Boot$150.0$69.0 -
Andrew Marc Men’s Eugene Ankle Boot$198.0$99.0 -
Lugz Men’s Convoy Lace-Up Boot$90.0$45.0 -
Andrew Marc Men’s Greenwich Lace-up Mid Boot$198.0$74.0 -
John Varvatos Men’s Hipster Chukka$198.0$99.0 -
Modern Vintage Men’s Alfred Lace-Up Boot$275.0$135.0 -
Sebago Men’s Westerly Lace-Up Boot$185.0$65.0 -
Ben Sherman Men’s Elmer Boot with Buckle$170.0$81.0 -
Ben Sherman Men’s Elmer Boot with Buckle$170.0$81.0 -
Donald J Pliner Men’s Bishop Chukka$240.0$130.0 -
Donald J Pliner Men’s Bishop Chukka$240.0$130.0 -
Donald J Pliner Men’s Bishop Chukka$240.0$130.0 -
Donald J Pliner Men’s Bishop Chukka$240.0$130.0 -
Florsheim Men’s Duane Chukka Boot$120.0$65.0 -
Wolverine Men’s Bento Moc Wedge Boot$170.0$95.0 -
Vince Camuto Men’s Sergio Cap Toe Double Gore Bootie$150.0$69.0 -
Vince Camuto Men’s Sergio Cap Toe Double Gore Bootie$150.0$69.0 -
Ben Sherman Men’s Leon Cap Toe Boot$175.0$84.0 -
Andrew Marc Men’s Greenwich Lace-up Mid Boot$198.0$74.0 -
Rockport Men’s Eastern Empire Plain Toe Chukka Boot$170.0$83.0 -
J Artola Men’s Dakota Lug Bottom Boot$325.0$83.0 -
J Artola Men’s Dakota Lug Bottom Boot$325.0$83.0 -
Calvin Klein Men’s Winston Boot with Buckle$150.0$69.0 -
Robert Wayne Men’s Harness Side Zip Boot$130.0$65.0 -
Robert Wayne Men’s Harness Side Zip Boot$130.0$65.0 -
Kenneth Cole Reaction Men’s Big Buck Boot$148.0$74.0 -
Kenneth Cole Reaction Men’s Big Buck Boot$148.0$74.0 -
Joseph Abboud Men’s Clint Chukka Boot$175.0$79.0 -
Andrew Marc Men’s Stanton Chukka$128.0$64.0 -
Joseph Abboud Men’s Winston Chukka Boot$125.0$60.0 -
G. H. Bass Men’s Reddington Boot$99.0$59.0 -
Robert Wayne Men’s Wingtip Lace Up Chukka$120.0$60.0 -
John Varvatos Men’s Redding Chukka$198.0$99.0 -
Rockport Men’s Break Trail Too Moc Mid Boot$200.0$94.0 -
Lugz Men’s Drifter Lace-Up Boot$82.0$40.0 -
Tommy Hilfiger Men’s Casual Boot$140.0$80.0 -
Joseph Abboud Men’s Chester Chelsea Boot$175.0$79.0 -
Tommy Hilfiger Men’s Marshall Boot$100.0$55.0 -
Sebago Men’s Coburn Mid Lace-Up Boot$180.0$65.0 -
Lugz Men’s Grant Chukka$80.0$42.0 -
Lugz Men’s Grant Chukka$80.0$42.0 -
Marc NY Men’s Hudson Chukka Boot$128.0$70.0 -
Tommy Hilfinger Men’s Holbrook Ankle Boot$140.0$80.0 -
Sebago Men’s Halyard Chukka Boot$185.0$65.0 -
G. H. Bass Men’s Redstone Boot$99.0$59.0 -
Steve Madden Men’s Kickit Chukka$100.0$49.0 -
Calvin Klein Men’s Flynn Navy New Suede Oxford 7.5 M$98.0$50.0 -
Moods of Norway Men’s Fana Boot$299.0$149.0 -
Joseph Abboud Men’s John Chukka Boot$175.0$79.0 -
Original Penguin Men’s Jerry Jeff Boot$180.0$90.0 -
Wolverine Men’s Shindell Boot$140.0$70.0 -
Sebago Men’s Coburn Mid Lace-Up Boot$180.0$65.0 -
Gordon Rush Men’s Bartlett Lace-up Boot$230.0$45.0
