37 items
  • Kindarumflex - Chelsea boot
    Flexsole
  • Jasperflex - Chelsea boot
    New
  • Gweracien - Chelsea boot
  • Druven - Chelsea boot
    Mr. B's Collection
  • 30% off sneakers
    Exclusions apply. Prices as shown.
  • Bruchsalflex-w - Chelsea boot
    Wide width
  • Karmelo - Chelsea boot
  • Karmelo - Chelsea boot
  • Criwien - Ankle boot
  • Criwien - Ankle boot
  • Bruchsalflex - Chelsea boot
    Flexsole
  • Darovflex - Chelsea boot
    Flexsole
  • Gweracien - Chelsea boot
  • Bruchsalflex - Chelsea boot
    Flexsole
  • Criwien - Ankle boot
  • Joshh - Chelsea boot
    New
  • Aboide - Chelsea boot
    Mr. B's Collection
  • Darovflex - Chelsea boot
    Flexsole
  • Etandari - Chelsea boot
    New
  • Etandari - Chelsea boot
    New
  • Jasperflex - Chelsea boot
    New
  • Gweracien - Chelsea boot
    New

Boot up in the sleek style and tailored sophistication of an iconic chelsea boot. The easiest way to slip into the cool weather season in style, these timeless ankle boots were designed to pair just as well with your laidback 'fits than with your formal wear. Opt for casual boots for everyday wear and strolls through the city, or pick a dressier boot for special occasions.

From luxe leather to rich suede, our assortment of chelsea boots for men also come equipped with special features such as waterproof construction or even slip-resistnat traction through chunky lug soles. All weather boots designed for weather, but made for style.