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Gone are the sandal wearing days of summer. Embrace fall with this collection of handsome chukkas and desert boots from some of our favorite brands. Balancing equal parts style with durability, this mix boasts classic ankle designs as well as boat shoe and sneaker-inspired elements. Pair any of these styles with cuffed chinos and a flannel button-down for a foolproof look this season.
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Tod’s Men’s Chukka (Ivory)$598$465.00 -
John Varvatos Men’s Hipster Chukka (Espresso)$475$299.00 -
Dino Bigioni Men’s Chukka Boot (Black Lama)$475$239.00 -
Dino Bigioni Men’s Chukka Boot (Brown Lama)$420$239.00 -
Gordon Rush Collection Men’s Taylor Chukka Boot (Brown Suede)$395$199.00 -
Mezlan Men’s Grosetto Boot (Brown)$425$198.00 -
The Generic Man Men’s Monkman Ankle Boot (Black)$425$191.00 -
The Generic Man Men’s Monkman Ankle Boot (Camel/Brown)$395$191.00 -
Mezlan Men’s Trinity Dress Boot (Burgundy)$310$169.00 -
The Generic Man Men’s Chuckman Leather Chukka (Black)$355$155.00 -
The Generic Man Men’s Florentine Suede Chukka (Black)$355$145.00 -
The Generic Man Men’s Florentine Suede Chukka (Green)$355$145.00 -
The Generic Man Men’s Florentine Suede Chukka (Indigo)$355$145.00 -
The Generic Man Men’s Florentine Suede Chukka (Red City)$350$145.00 -
Rogue Men’s Rycroft Chukka Boot (Red)$310$139.00 -
The Generic Man Men’s Chuckman Suede Chukka (Green/Brown)$310$134.00 -
The Generic Man Men’s Chuckman Suede Chukka (Indigo/Brown)$310$134.00 -
The Generic Man Men’s Chuckman Suede Chukka (Red City/Brown)$215$134.00 -
Bacco Bucci Men’s Gonzalo Boot (Black)$215$109.00 -
Bacco Bucci Men’s Gonzalo Boot (Brown)$245$109.00 -
Bacco Bucci Men’s Gabriele Boot (Black)$245$109.00 -
Bacco Bucci Men’s Gabriele Boot (Brown)$275$109.00 -
Rogue Men’s Bradbury Lace-Up (Camel)$196$109.00 -
J SHOES Men’s Monarch Lace-Up Boot (Black)$196$99.00 -
J SHOES Men’s Monarch Lace-Up Boot (Milkshake/Mid Brown)$228$99.00 -
John Varvatos Men’s Sid Softy Chukka (Moss)$163$99.00 -
J SHOES Men’s Mojave Boot (Black)$145$79.00 -
Florsheim Men’s Tienomite Mid Boat Shoe (Brown)$145$79.00 -
Florsheim Men’s Tienomite Mid Boat Shoe (Navy)$215$79.00 -
J. Artola Men’s Brandon MX Chukka (Dark Brown)$150$75.00 -
Generic Surplus Men’s Ledger Crepe Boot (Black)$150$75.00 -
Generic Surplus Men’s Ledger Crepe Boot (Monks Robe)$235$75.00 -
adidas SLVR Men’s Desert Lace-Up Boot (Beech/Egret/Beech)$180$70.00 -
Dr. Martens Men’s Chester Boot (Navy)$170$69.00 -
J. Artola Men’s Brandon Fx Chukka Boot (Grey)$170$69.00 -
J. Artola Men’s Brandon Fx Chukka Boot (Navy)$130$69.00 -
Calvin Klein Men’s Wilson Boot (Charcoal Suede)$130$65.00 -
Calvin Klein Men’s Wilson Boot (Dark Brown)$130$65.00 -
Calvin Klein Men’s Wilson Boot (Navy Suede)$130$65.00 -
Calvin Klein Men’s Wilson Boot (Stone Suede)$140$65.00 -
Calvin Klein Men’s Smith Ankle Boot (Black)$150$65.00 -
J SHOES Men’s Volunteer Fab Boot (Black/Grey)$125$64.00 -
Rockport Men’s Empire West Chukka Boot (Bitter Chocolate Suede)$125$62.00 -
Rockport Men’s Empire West Chukka Boot (British Tan)$125$62.00 -
Rockport Men’s Empire West Chukka Boot (Grey Suede)$145$62.00 -
Rockport Men’s Ledge Hill Lace-Up Boot (Bitter Chocolate Suede)$140$59.00 -
Calvin Klein Men’s Smith Suede Boot (Dark Brown)$100$59.00 -
Steve Madden Men’s Kickit Chukka (Tan)$190$59.00 -
WeSC Men’s Gilliam Shoe (Beluga)$190$57.00 -
WeSC Men’s Gilliam Shoe (Walnut Brown)$130$57.00 -
Sebago Men’s Beacon Chukka (Brown)$130$49.00 -
Sebago Men’s Beacon Chukka (Brown Oiled Waxy)$165$49.00 -
WeSC Men’s Lawrence Chukka (Beluga)$149$49.00 -
JD Fisk Men’s Henri Ankle Boot (Sand Canvas)$149$44.00 -
JD Fisk Men’s Henri Ankle Boot (Taupe Canvas)$140$44.00 -
Geox Men’s Juan Chukka (Beige)$130$39.00 -
Generic Surplus Men’s Dom Leather Boot (Black)$85$39.00 -
Bed|Stü Men’s Uncle Dowell Chukka (Black)$$32.00 -
Generic Surplus Men’s Dom Chukka (Brown)$$32.00 -
Generic Surplus Men’s Dom Chukka (Military Green/Mood Indigo)$$32.00
