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Wardrobe Refresh: Chukkas & Boots!
There comes a time when your basic sneakers need backup. Grab something sturdy to navigate slippery streets and stormy forecasts: This collection of boots and chukkas includes everything from rugged lace-ups to polished pull-ons. Just as comfortable as your dependable kicks, but more all-weather ready.

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  • Wolverine No. 1883 Men's Rowan 1000 Mile Lace-up Boot (Brown)


    Wolverine No. 1883 Men’s Rowan 1000 Mile Lace-up Boot (Brown)

    $450$229.00

  • The Generic Man Men's Riderman Chukka (Brown)


    The Generic Man Men’s Riderman Chukka (Brown)

    $430$225.00

  • The Generic Man Men's Riderman Chukka (Grey)


    The Generic Man Men’s Riderman Chukka (Grey)

    $430$225.00

  • Wolverine No. 1883 Men's Latham 1000 Mile Chukka (Rust)


    Wolverine No. 1883 Men’s Latham 1000 Mile Chukka (Rust)

    $390$199.00

  • Wolverine No. 1883 Men's Latham 1000 Mile Chukka (Beige)


    Wolverine No. 1883 Men’s Latham 1000 Mile Chukka (Beige)

    $390$199.00

  • Modern Fiction Men's Chelsea Boot (Charcoal)


    Modern Fiction Men’s Chelsea Boot (Charcoal)

    $398$189.00

  • Modern Fiction Men's Chelsea Boot (Stone)


    Modern Fiction Men’s Chelsea Boot (Stone)

    $398$189.00

  • Modern Fiction Men's Brogue Boot (Black)


    Modern Fiction Men’s Brogue Boot (Black)

    $398$189.00

  • Modern Fiction Men's Brogue Boot (Brown)


    Modern Fiction Men’s Brogue Boot (Brown)

    $398$189.00

  • The Generic Man Men's Chuckman Chukka Sneaker (Baby Blue)


    The Generic Man Men’s Chuckman Chukka Sneaker (Baby Blue)

    $305$169.00

  • The Generic Man Men's Chuckman Chukka Sneaker (Olive Green)


    The Generic Man Men’s Chuckman Chukka Sneaker (Olive Green)

    $305$169.00

  • The Generic Man Men's Chuckman Chukka Sneaker (Orange)


    The Generic Man Men’s Chuckman Chukka Sneaker (Orange)

    $305$169.00

  • Wolverine No. 1883 Men's Russell Field Boot (Tan)


    Wolverine No. 1883 Men’s Russell Field Boot (Tan)

    $320$159.00

  • Wolverine No. 1883 Men's Rockford 1000 Mile Lace-up Boot (Black)


    Wolverine No. 1883 Men’s Rockford 1000 Mile Lace-up Boot (Black)

    $400$159.00

  • The Generic Man Men's Florentine Chukka (Baby Blue)


    The Generic Man Men’s Florentine Chukka (Baby Blue)

    $340$149.00

  • The Generic Man Men's Florentine Chukka (Black)


    The Generic Man Men’s Florentine Chukka (Black)

    $340$149.00

  • J Artola Men's Emerson Lace Up Boot (Black)


    J Artola Men’s Emerson Lace Up Boot (Black)

    $295$149.00

  • J Artola Men's Emerson Lace Up Boot (Cognac)


    J Artola Men’s Emerson Lace Up Boot (Cognac)

    $295$149.00

  • J Artola Men's Emerson Lace Up Boot (Dark Brown)


    J Artola Men’s Emerson Lace Up Boot (Dark Brown)

    $295$149.00

  • Dr. Martens Men's Hambleton II Chukka (Charcoal)


    Dr. Martens Men’s Hambleton II Chukka (Charcoal)

    $225$149.00

  • Dr. Martens Men's Hambleton II Chukka (Dark Navy)


    Dr. Martens Men’s Hambleton II Chukka (Dark Navy)

    $225$149.00

  • Dr. Martens Men's Hambleton II Chukka (Tan)


    Dr. Martens Men’s Hambleton II Chukka (Tan)

    $225$149.00

  • Wolverine No. 1883 Men's Burton Lace-up Boot (Black)


    Wolverine No. 1883 Men’s Burton Lace-up Boot (Black)

    $300$149.00

  • Wolverine No. 1883 Men's Wyatt 1000 Mile Chukka (Navy)


    Wolverine No. 1883 Men’s Wyatt 1000 Mile Chukka (Navy)

    $300$149.00

  • Wolverine No. 1883 Men's Winchester Brogue Boot (Tan)


    Wolverine No. 1883 Men’s Winchester Brogue Boot (Tan)

    $350$145.00

  • Rogue Men's Platon Boot (Grey)


    Rogue Men’s Platon Boot (Grey)

    $275$138.00

  • Modern Fiction Men's Relaxed Chukka Boot (Brown)


    Modern Fiction Men’s Relaxed Chukka Boot (Brown)

    $288$129.00

  • Modern Fiction Men's Relaxed Chukka Boot (Stone)


    Modern Fiction Men’s Relaxed Chukka Boot (Stone)

    $288$129.00

  • Rogue Men's William Boot (Antiqued Camel)


    Rogue Men’s William Boot (Antiqued Camel)

    $250$119.00

  • Rogue Men's William Boot (Oxblood)


    Rogue Men’s William Boot (Oxblood)

    $250$119.00

  • Rogue Men's William Boot (Camel)


    Rogue Men’s William Boot (Camel)

    $250$119.00

  • Modern Fiction Men's Casual Chukka Boot (Charcoal)


    Modern Fiction Men’s Casual Chukka Boot (Charcoal)

    $315$109.00

  • Modern Fiction Men's Casual Chukka Boot (Tan)


    Modern Fiction Men’s Casual Chukka Boot (Tan)

    $315$109.00

  • Bacco Bucci Men's Gonzalo Boot (Black)


    Bacco Bucci Men’s Gonzalo Boot (Black)

    $215$108.00

  • J SHOES Men's Monarch Lace-Up Boot (Cobble Stone)


    J SHOES Men’s Monarch Lace-Up Boot (Cobble Stone)

    $196$99.00

  • J SHOES Men's Monarch Lace-Up Boot (Fox/Mid Brown)


    J SHOES Men’s Monarch Lace-Up Boot (Fox/Mid Brown)

    $196$99.00

  • Dino Bigioni Men's Desert Boot (Electric Blue)


    Dino Bigioni Men’s Desert Boot (Electric Blue)

    $375$99.00

  • Dino Bigioni Men's Desert Boot (Light Tan)


    Dino Bigioni Men’s Desert Boot (Light Tan)

    $375$99.00

  • Broken Homme Men's Robert Boot (Black/Black Solid)


    Broken Homme Men’s Robert Boot (Black/Black Solid)

    $299$99.00

  • Sebago Men's Pinehurst Boot (Black)


    Sebago Men’s Pinehurst Boot (Black)

    $215$99.00

  • Sebago Men's Pinehurst Boot (Brown)


    Sebago Men’s Pinehurst Boot (Brown)

    $215$99.00

  • Original Penguin Men's Jerry Jeff Lace-Up Boot (Black Distressed)


    Original Penguin Men’s Jerry Jeff Lace-Up Boot (Black Distressed)

    $168$89.00

  • Andrew Marc Men's Dorchester Chukka Boot (Espresso/Black/Deep Natural Suede)


    Andrew Marc Men’s Dorchester Chukka Boot (Espresso/Black/Deep Natural Suede)

    $178$89.00

  • Dr. Martens Men's Marcus Brogue Lace-Up Boot (Desert Star/Tan/Brando Waxy Canvas)


    Dr. Martens Men’s Marcus Brogue Lace-Up Boot (Desert Star/Tan/Brando Waxy Canvas)

    $180$89.00

  • Andrew Marc Men's Dorchester Chukka (Med Blue)


    Andrew Marc Men’s Dorchester Chukka (Med Blue)

    $178$89.00

  • Andrew Marc Men's Dorchester Chukka (Veridian)


    Andrew Marc Men’s Dorchester Chukka (Veridian)

    $178$89.00

  • J Artola Men's Jerry Casual Chukka (Dusty Pink)


    J Artola Men’s Jerry Casual Chukka (Dusty Pink)

    $175$89.00

  • J Artola Men's Jerry Casual Chukka (Electric Blue)


    J Artola Men’s Jerry Casual Chukka (Electric Blue)

    $175$89.00

  • J Artola Men's Jerry Casual Chukka (Mustard)


    J Artola Men’s Jerry Casual Chukka (Mustard)

    $175$89.00

  • J Artola Men's Jerry Casual Chukka (Natural)


    J Artola Men’s Jerry Casual Chukka (Natural)

    $175$89.00

  • J SHOES Men's Escape Chukka (Cork)


    J SHOES Men’s Escape Chukka (Cork)

    $184$89.00

  • Sebago Men's Tremont Boot (Black)


    Sebago Men’s Tremont Boot (Black)

    $155$86.00

  • Sebago Men's Tremont Boot (Brown)


    Sebago Men’s Tremont Boot (Brown)

    $155$86.00

  • J SHOES Men's Volunteer Chukka (Black)


    J SHOES Men’s Volunteer Chukka (Black)

    $150$79.00

  • J SHOES Men's Volunteer Chukka (Dark Brown)


    J SHOES Men’s Volunteer Chukka (Dark Brown)

    $150$79.00

  • Tretorn Men's Holdyn Leather Boot (Black)


    Tretorn Men’s Holdyn Leather Boot (Black)

    $150$79.00

  • Tretorn Men's Holdyn Leather Boot (Chocalate Brown)


    Tretorn Men’s Holdyn Leather Boot (Chocalate Brown)

    $150$79.00

  • Rockport Men's TruWalk Zero II Chukka Boot (Dark Brown Suede)


    Rockport Men’s TruWalk Zero II Chukka Boot (Dark Brown Suede)

    $128$79.00

  • Rockport Men's Dialed In Zipper Boot (British Tan)


    Rockport Men’s Dialed In Zipper Boot (British Tan)

    $140$79.00

  • Andrew Marc Men's Stanton Suede Chukka (Navy/Charcoal)


    Andrew Marc Men’s Stanton Suede Chukka (Navy/Charcoal)

    $140$79.00

  • Ben Sherman Men's Aberdeen Leather Chukka (Black)


    Ben Sherman Men’s Aberdeen Leather Chukka (Black)

    $138$69.00

  • Ben Sherman Men's Aberdeen Leather Chukka (Blue)


    Ben Sherman Men’s Aberdeen Leather Chukka (Blue)

    $155$69.00

  • Ben Sherman Men's Aberdeen Leather Chukka (Grey)


    Ben Sherman Men’s Aberdeen Leather Chukka (Grey)

    $135$69.00

  • Rockport Men's Dialed In Chukka Boot (Bitter Chocolate Suede)


    Rockport Men’s Dialed In Chukka Boot (Bitter Chocolate Suede)

    $130$69.00

  • Rockport Men's Dialed In Chukka Boot (Black)


    Rockport Men’s Dialed In Chukka Boot (Black)

    $125$69.00

  • SeaVees Men's Bayside Chukka (Black/Pigskin Suede)


    SeaVees Men’s Bayside Chukka (Black/Pigskin Suede)

    $128$69.00

  • Rockport Men's Ledge Hill WP Chukka Boot (Dark Vicuna)


    Rockport Men’s Ledge Hill WP Chukka Boot (Dark Vicuna)

    $128$65.00

  • Generic Surplus Men's Dom Chukka (Brown)


    Generic Surplus Men’s Dom Chukka (Brown)

    $145$59.00

  • Ben Sherman Men's Aberdeen Chukka Boot (Chocolate)


    Ben Sherman Men’s Aberdeen Chukka Boot (Chocolate)

    $145$55.00

  • Sebago Men's Campsides Mid Oxford (Chocolate)


    Sebago Men’s Campsides Mid Oxford (Chocolate)

    $90$55.00

  • SeaVees Men's Bayside Moccasin (Rust Brushed Twill)


    SeaVees Men’s Bayside Moccasin (Rust Brushed Twill)

    $135$55.00

  • SeaVees Men's Bayside Moccasin (Slate Navy Brushed Twill)


    SeaVees Men’s Bayside Moccasin (Slate Navy Brushed Twill)

    $135$55.00

  • Seavees Men's 04/60 Two Eye Floater Chukka (Flax Suede)


    Seavees Men’s 04/60 Two Eye Floater Chukka (Flax Suede)

    $85$55.00

  • Seavees Men's 04/60 Two Eye Floater Chukka (Ink Suede)


    Seavees Men’s 04/60 Two Eye Floater Chukka (Ink Suede)

    $60$55.00

  • Florsheim Men's Tienomite Mid Boat Shoe (Dark Cherry)


    Florsheim Men’s Tienomite Mid Boat Shoe (Dark Cherry)

    $60$49.00

  • Florsheim Men's Tienomite Mid Boat Shoe (Navy)


    Florsheim Men’s Tienomite Mid Boat Shoe (Navy)

    $130$49.00

  • Tretorn Otto Mid Suede Sneaker Boot (Chocolate Brown)


    Tretorn Otto Mid Suede Sneaker Boot (Chocolate Brown)

    $79$49.00

  • Generic Surplus Men's Ledger Mid Boot (Black)


    Generic Surplus Men’s Ledger Mid Boot (Black)

    $79$45.00

  • Generic Surplus Men's Ledger Mid Boot (Earth)


    Generic Surplus Men’s Ledger Mid Boot (Earth)

    $175$45.00

  • Bed|Stü Men's Uncle Dowell Chukka Boot (Black)


    Bed|Stü Men’s Uncle Dowell Chukka Boot (Black)

    $$39.00

  • Nautica Men's Del Mar Mid Boat Shoe (Denim)


    Nautica Men’s Del Mar Mid Boat Shoe (Denim)

    $$39.00

  • Nautica Men's Del Mar Mid Boat Shoe (Tan)


    Nautica Men’s Del Mar Mid Boat Shoe (Tan)

    $$39.00

  • Generic Surplus Men's Dom Leather Boot (Black)


    Generic Surplus Men’s Dom Leather Boot (Black)

    $$39.00

  • Generic Surplus Men's McNairy Chukka Sneaker (Dark Navy)


    Generic Surplus Men’s McNairy Chukka Sneaker (Dark Navy)

    $$39.00

  • Generic Surplus Men's McNairy Chukka Sneaker (Sand)


    Generic Surplus Men’s McNairy Chukka Sneaker (Sand)

    $$39.00

  • Rogue Men's Hawthorne Lowrise Boot (Dark Grey)


    Rogue Men’s Hawthorne Lowrise Boot (Dark Grey)

    $$35.00

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