98 items
  • Campero - Ankle Boot
    New
  • Verdu - Slippers
    New
  • Rambler - Hiking boot
    Premium Selection
  • Massinger - Slippers
    New
  • Get It For The Holidays
    Order by 12/17 for delivery before 12/24 + enjoy FREE shipping!
  • Peak - Combat ankle boot
    Premium Selection
  • Datatine - Chelsea boot
    Lightweight
  • Yireni - Ankle boot
    New
  • Nomadic - Chelsea boot
    Premium Selection
  • Yireni - Ankle boot
    New
  • Peak - Combat ankle boot
    Premium Selection
  • Preralith - Lace-up boot
    Waterproof
  • Preralith - Lace-up boot
    Waterproof
  • Yonathan-wp - Combat ankle boot
    Waterproof
  • Decius - Chelsea boot
    Slip Resistant
  • Tewdor - Lace-up boot
    Waterproof
  • Ashdale - Chukka boot
    Slip Resistant
  • Moyston - Lace-up boot
    Waterproof
  • Tewdor - Lace-up boot
    Waterproof
  • Moyston - Lace-up boot
    Waterproof
  • Nomadic - Chelsea boot
    Premium Selection
  • Preralith - Lace-up boot
    Waterproof

Take it easy with effortlessly cool casual boots for men designed to pair seamlessly with your most laidback looks. For an outfit that's casual yet still put together, consider quintessential chelsea boots and chinos to do the trick. Looking for something that's a little off-duty? Opt for wear-anywhere lace-up boots or chunky boots with leather exteriors and treaded outsoles to pull off a modern yet rugged look. For more relaxed, day-to-day 'fits, pair our chukka boots with jeans and a crew neck sweatshirt and you'll be set for lunch meetings and errands alike. No matter your personal style, these casual ankle boots have got you covered.

When the cool season sets in, weather out any storm with our assortment of weather-ready boots built to combat the elements in style. Casual, sleek and extra functional, these winter boots and waterproof boots boast several features such as slip-resistant traction and water-repelling coating to ensure your feet stay grounded and warm, all the time.