From cool relaxed suede to classic leather, these timeless chelsea boots are wardrobe must-haves.

34 items
  • Dannie - Ankle boot
    Now 30% off!
  • Biondi-r - Chelsea ankle boot
    Excluded from promotion
  • Palainseven - Chelsea boot
    Now 30% off!
  • FREE Holiday shipping on all orders🎁
    Order by 12/15 for guaranteed delivery by 12/24.
  • Biondi-r - Chelsea ankle boot
    Excluded from promotion
  • Biondi-r - Chelsea ankle boot
    Excluded from promotion
  • Vianello-r - Chelsea ankle boot
    Excluded from promotion
  • Winter Sale

    30% OFF
    select boots & handbags

    Prices as shown. Exclusions apply.
  • Bentworth black by Aldo Shoes - Main
    Now 30% off!
  • Bentworth brown by Aldo Shoes - Main
    Now 30% off!
  • Relari - Chelsea boot
    Now 30% off!
  • Vianello-r - Chelsea ankle boot
    Now 30% off!
  • Biondi-r - Chelsea ankle boot
    Excluded from promotion
  • Bentworth beige by Aldo Shoes - Main
    Now 30% off!
  • Anewen - Chelsea boot
    Now 30% off!
  • Larerin - Chelsea ankle boot
    Now 30% off!
  • Larerin - Chelsea ankle boot
    Now 30% off!
  • Gweracien - Chelsea boot
    Excluded from promotion
  • Wadda - Chelsea boot
    Now 30% off!
  • Eraurwen - Chelsea boot
    Now 30% off!
  • Gregiori - Chelsea boot
    Now 30% off!

From sleek leather to luxe suede, these timeless chelsea boots inject comfort and ease in every step. Whether you're looking to dress up or down, these ankle boots pair with literally everything. Wear them with a plaid trousers and ribbed turtleneck for a vintage-inspired look or with a denim jacket and ripped jeans for an off-duty style boost.

Crafted in rich materials such as leather and suede, these chelsea boots for men boast minimal appeal and tailored sophistication.