We may earn money or products from the companies mentioned in this post.

Buy Fall Refresh: Men's Chukka & Chelsea Boots!

more >>

Fall Refresh: Men’s Chukka & Chelsea Boots

  • Spencer Black F/G Leather Chukka Boot

    Walk-Over Spencer Black F/G Leather Chukka Boot

    $99.0, $39.97

  • Spencer Desert Taupe F/G Leather Chukka Boot

    Walk-Over Spencer Desert Taupe F/G Leather Chukka Boot

    $99.0, $39.97

  • Roy Moc Toe Boot

    Walk-Over Roy Moc Toe Boot

    $130.0, $69.97

  • Sebastian Perforated Shoe

    Walk-Over Sebastian Perforated Shoe

    $139.95, $69.97

  • Bushacre 2 Suede Chukka Boot

    Walk-Over Bushacre 2 Suede Chukka Boot

    $100.0, $69.97

  • Dysoto Plain Toe Chukka Boot

    Walk-Over Dysoto Plain Toe Chukka Boot

    $80.0, $49.97

  • Seattle Chukka Boot

    Walk-Over Seattle Chukka Boot

    $80.0, $44.97

  • Seattle Chukka Boot

    Walk-Over Seattle Chukka Boot

    $80.0, $44.97

  • Morgan Lace-Up Chukka Boot

    Walk-Over Morgan Lace-Up Chukka Boot

    $329.99, $79.97

  • Morgan Lace-Up Chukka Boot

    Walk-Over Morgan Lace-Up Chukka Boot

    $329.99, $79.97

  • Morgan Lace-Up Chukka Boot

    Walk-Over Morgan Lace-Up Chukka Boot

    $329.99, $79.97

  • Leather Chukka Boot

    Walk-Over Leather Chukka Boot

    $129.0, $79.97

  • Bangor Chukka Boot

    Walk-Over Bangor Chukka Boot

    $75.0, $39.97

  • Bangor Chukka Boot

    Walk-Over Bangor Chukka Boot

    $75.0, $39.97

  • Rhodes Cap Toe Chukka Boot

    Walk-Over Rhodes Cap Toe Chukka Boot

    $75.0, $44.97

  • Rhodes Cap Toe Chukka Boot

    Walk-Over Rhodes Cap Toe Chukka Boot

    $75.0, $44.97

  • Hutchins Chelsea Boot

    Walk-Over Hutchins Chelsea Boot

    $160.0, $69.97

  • Hutchins Chelsea Boot

    Walk-Over Hutchins Chelsea Boot

    $160.0, $69.97

  • Parson Chelsea Boot

    Walk-Over Parson Chelsea Boot

    $124.0, $49.97

  • Oregon Leather Chelsea Boot

    Walk-Over Oregon Leather Chelsea Boot

    $120.0, $39.97

  • Hip & Bone Chelsea Boot (Men)

    Walk-Over Hip & Bone Chelsea Boot (Men)

    $310.0, $119.97

  • Hip & Bone Chelsea Boot (Men)

    Walk-Over Hip & Bone Chelsea Boot (Men)

    $310.0, $119.97

  • Kory Chelsea Boot

    Walk-Over Kory Chelsea Boot

    $375.0, $179.97

  • Mayport Boot

    Walk-Over Mayport Boot

    $80.0, $39.97

  • Crepe Chukka Boot

    Walk-Over Crepe Chukka Boot

    $465.0, $179.97

  • Crepe Chukka Boot

    Walk-Over Crepe Chukka Boot

    $465.0, $179.97

  • Chukka Boot

    Walk-Over Chukka Boot

    $129.0, $69.97

  • Leather Chukka Boot

    Walk-Over Leather Chukka Boot

    $98.0, $59.97

  • Chukka Waterproof Leather Boot

    Walk-Over Chukka Waterproof Leather Boot

    $129.95, $79.97

  • Leather Chukka Boot

    Walk-Over Leather Chukka Boot

    $129.95, $79.97

  • Dysoto Textured Chukka Boot

    Walk-Over Dysoto Textured Chukka Boot

    $80.0, $49.97

  • Curington Top Leather Ankle Boot

    Walk-Over Curington Top Leather Ankle Boot

    $110.0, $69.97

  • Castellano Chukka Boot

    Walk-Over Castellano Chukka Boot

    $140.0, $79.97

  • Charcoal Fleck Chukka Boot

    Walk-Over Charcoal Fleck Chukka Boot

    $98.0, $54.97

  • Hardwood Leather Chukka Boot

    Walk-Over Hardwood Leather Chukka Boot

    $240.0, $99.97

  • Neuman Leather Chukka Boot

    Walk-Over Neuman Leather Chukka Boot

    $185.0, $79.97

  • Bowie Leather Chukka Boot

    Walk-Over Bowie Leather Chukka Boot

    $210.0, $89.97

  • Drover Ice + Waterproof TX Leather Chukka Boot

    Walk-Over Drover Ice + Waterproof TX Leather Chukka Boot

    $69.97, $69.97

  • Pegaso Suede Chukka Boot

    Walk-Over Pegaso Suede Chukka Boot

    $195.0, $89.97

  • Neuman Leather Chukka Boot

    Walk-Over Neuman Leather Chukka Boot

    $185.0, $79.97

  • Rebowie Leather Chukka Boot

    Walk-Over Rebowie Leather Chukka Boot

    $220.0, $99.97

  • Boot-Up Chukka - Wide Width Available

    Walk-Over Boot-Up Chukka – Wide Width Available

    $220.0, $109.97

  • IM 12 Plain Toe Genuine Shearling Boot

    Walk-Over IM 12 Plain Toe Genuine Shearling Boot

    $278.0, $99.97

  • Elude Waterproof Suede Chukka Boot

    Walk-Over Elude Waterproof Suede Chukka Boot

    $130.0, $59.97

  • Vanek Rise Mid-Top Leather Boot

    Walk-Over Vanek Rise Mid-Top Leather Boot

    $100.0, $59.97

  • Deia Leather Chukka

    Walk-Over Deia Leather Chukka

    $235.0, $79.97

  • Storm Chelsea Waterproof Boot

    Walk-Over Storm Chelsea Waterproof Boot

    $200.0, $99.97

  • Alexander Chukka Boot

    Walk-Over Alexander Chukka Boot

    $276.0, $109.97

  • Morrys Leather Chukka Boot

    Walk-Over Morrys Leather Chukka Boot

    $199.0, $89.97

  • Guardi Boot

    Walk-Over Guardi Boot

    $230.0, $119.97

  • Jamie Chelsea Boot

    Walk-Over Jamie Chelsea Boot

    $198.0, $94.97

  • Morrys Leather Chukka Boot

    Walk-Over Morrys Leather Chukka Boot

    $199.0, $89.97

  • Boot-Up Chukka - Wide Width Available

    Walk-Over Boot-Up Chukka – Wide Width Available

    $220.0, $109.97

  • Durango Wingtip Chelsea Boot

    Walk-Over Durango Wingtip Chelsea Boot

    $295.0, $139.97

  • Durango Wingtip Chelsea Boot

    Walk-Over Durango Wingtip Chelsea Boot

    $295.0, $139.97

  • Pilot Suede Chukka

    Walk-Over Pilot Suede Chukka

    $245.0, $69.97

  • Pilot Suede Chukka

    Walk-Over Pilot Suede Chukka

    $245.0, $64.97

  • Thatcher Chukka Boot

    Walk-Over Thatcher Chukka Boot

    $335.0, $149.97

  • Waldorf Chukka Boot

    Walk-Over Waldorf Chukka Boot

    $375.0, $179.97

  • Lombardo Stitched Boot

    Walk-Over Lombardo Stitched Boot

    $220.0, $99.97

  • Monarch Plus Chukka Boot

    Walk-Over Monarch Plus Chukka Boot

    $198.0, $94.97

  • Scafati Chelsea Sneaker

    Walk-Over Scafati Chelsea Sneaker

    $125.0, $59.97

  • Scafati Chelsea Sneaker

    Walk-Over Scafati Chelsea Sneaker

    $125.0, $59.97

  • Strider LX Sneaker

    Walk-Over Strider LX Sneaker

    $65.0, $29.97

  • Domus Leather High-Top Sneaker

    Walk-Over Domus Leather High-Top Sneaker

    $190.0, $79.97

: Men