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  • $59.97 sale
    $100.00 Reg.

    Columbia Newton Ridge Plus II Waterproof Men's Hiking Boots

  • $170.00

    Timberland PRO Direct Attach Men's Waterproof 6-in. Work Boots

  • $59.97 sale
    $100.00 Reg.

    Columbia Newton Ridge Plus II Men's Waterproof Hiking Boots

  • $59.99

    Sonoma Goods For Life® Ledger Men's Chukka Boots

  • $65.00 - $100.00
    $100.00 Reg.

    Skechers Relaxed Fit® Respected Boswell Men's Boots

  • $110.00

    Caterpillar Threshold Men's Waterproof Steel Toe Work Boots

  • $125.00

    Timberland PRO Gritstone Men's Steel-Toe Work Boots

  • $250.00

    Thorogood American Heritage Men's Moc-Toe Work Boots

  • $59.49 sale
    $84.99 Reg.

    Vance Co. Landon Men's Chelsea Boots

  • $89.99

    Caterpillar Striver Men's Steel Toe Leather Work Boots

  • $86.25 sale
    $115.00 Reg.

    Georgia Boots Brookville Men's 6-in. Waterproof Work Boots

  • For Price, Add to Cart

    $80.00 Reg.

    Dr. Scholl's Charge Men's Slip-Resistant Ankle Work Boots

  • $120.00

    Wolverine Floorhand Men's Steel Toe Waterproof Work Boots

    (8)
  • $85.00

    Nunn Bush® Tour Work Men's Sneaker Boots

    (4)
  • $112.50 - $128.25 sale
    $150.00 - $171.00 Reg.

    Georgia Boots Men's 6-in. Wedge Work Boots

  • $55.97 sale
    $75.00 Reg.

    Northside Hargrove Mid Men's Waterproof Hiking Boots

    Closeout Deal
  • $135.00 - $151.50 sale
    $180.00 - $202.00 Reg.

    Georgia Boots AMP LT Men's Wedge Waterproof Ankle Work Boots

  • $59.49 sale
    $84.99 Reg.

    Vance Co. Franco Men's Plain Toe Chukka Boots

  • $132.75 - $140.25 sale
    $177.00 - $187.00 Reg.

    Georgia Boots Farm & Ranch Lacer Men's 8-in. Work Boots

  • Top Rated
    $250.00

    Thorogood American Heritage Men's Work Boots

  • $69.99 sale
    $99.99 Reg.

    Vance Co. Marshall Men's Chelsea Boots

  • $51.99 sale
    $65.00 Reg.

    Northside Gresham Mid Men's Waterproof Hiking Boots

  • $62.97 sale
    $85.00 Reg.

    Eddie Bauer Clydehil Men's Waterproof Hiking Boots

  • $105.00 sale
    $140.00 Reg.

    Georgia Boots Farm & Ranch Men's Wedge Chukka Boots

  • $156.00 sale
    $208.00 Reg.

    Georgia Boots Fixpoint Men's 6-in. Waterproof Work Boots

  • $99.95

    Propet Seeley II Men's Composite-Toe Work Shoes

  • $74.97 sale
    $100.00 Reg.

    Skechers® Relaxed Fit® Relment Traven Men's Waterproof Boots

  • $87.47

    Propet Traverse Men's Waterproof Hiking Boots

  • $115.49 sale
    $164.99 Reg.

    Thomas & Vine Aldridge Men's Leather Chukka Boots

    (6)
  • $114.95

    Propet Ridge Walker Men's Waterproof Hiking Boots

  • $129.00 sale
    $172.00 Reg.

    Georgia Boots Eagle One Men's Waterproof Steel Toe Chelsea Work Boots

  • $55.99 sale
    $79.99 Reg.

    Vance Co. Alex Men's Cap-Toe Dress Boots

  • $125.25 sale
    $167.00 Reg.

    Georgia Boots Eagle One Men's Waterproof Chelsea Work Boots

  • $95.00

    Nunn Bush® Otto Men's Suede Chukka Boots

    Closeout Deal
  • $90.00

    Nunn Bush® Chase Men's Boots

    (1)
  • $54.99 sale
    $60.00 Reg.

    Deer Stags Bangor Men's Chukka Boots

  • $295.00

    Thorogood American Heritage Men's Waterproof Safety-Toe Work Boots

    (6)
  • Top Rated
    $285.00

    Thorogood American Heritage Men's Waterproof Safety-Toe Work Boots

  • $280.00

    Thorogood American Heritage Men's Waterproof Work Boots

  • $132.99 sale
    $189.99 Reg.

    Thomas & Vine Kairo Tru Comfort Foam Cap Toe Men's Ankle Boot

  • $63.75 sale
    $85.00 Reg.

    Dockers Brookside Men's Boots

    (3)
  • $54.99 sale
    $60.00 Reg.

    Deer Stags Rockland Men's Chelsea Boots

  • $59.97 sale
    $79.99 Reg.

    Madden Daqost Men's Boots

  • $115.00

    Wolverine Floorhand Moc Toe Men's Waterproof Work Boots

  • $115.00

    Nunn Bush® 1912 Men's Leather Ankle Boots

    (7)
  • $114.95

    Propet Findley Men's Suede Chukka Boots

  • $114.95

    Propet Cliff Walker Men's Waterproof Hiking Boots

  • $111.99 sale
    $159.99 Reg.

    Thomas & Vine Jarett Men's Wingtip Ankle Boots

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Men’s Ankle Boots

Ankle boots are a great addition to any man's wardrobe. A versatile footwear choice, they're both comfortable and stylish. You can find men's ankle boots that are casual as well as dressier styles. With ankle boots from Exdup, you'll be prepared for any occasion!

Shop Exdup for shoes and footwear for the entire family, including our selection of men’s ankle boots! You can also find athletic and active shoes, dress shoes, sandals, and more, all available for men, women, and kids, too!

Styles of Men’s Ankle Boots

Exdup offers a variety of men's ankle boots designed to fit into your everyday look. No matter if you need a casual, laid-back pair of boots, or a dressy, classic set of footwear, we have you covered! Let’s look at boot styles you’re sure to consider:

  • Chelsea

Men’s Chelsea boots have certain characteristics that set them apart from other men’s footwear. Chelsea boots feature a shaft that hits at ankle height or slightly above it. They also feature rounded toes and low heels. Chelsea boots should fit relatively snug around the foot, but do offer elastic side panels for flexibility. Chelsea boots might also feature a zipper or standard shoelaces.

To get the most out of your pair of Chelsea boots, pick up a pair in brown. This color option allows for the most versatility, as they can more easily be dressed up or dressed down. Brown Chelsea boots coordinate with everything from men’s suits to jeans and khakis.

  • Chukka

Chukka boots are a classic style of men’s footwear, and they present a fashionable yet casual look. Chukka boots are more casual than Chelsea boots and have distinctive features such as eyelets and laces. But they’re nice enough to wear for many different occasions, including the workplace. This versatility makes chukka boots ideal for any man’s footwear collection.

  • Slip-On Work Boots

When it comes to wearing to work, men’s slip-on boots can fit the bill if you’re heading to an office or a construction site. Rugged waterproof slip-on boots keep your feet comfortable in a wide range of conditions, and some workwear boots offer extra safety features like steel toes and extra traction.

Brands of Men’s Ankle Boots

For a casual, rugged look opt for a pair of men's Timberland boots. These ankle boots are great for hiking and showcasing your outdoorsy style. Many men's snow boots are simply an ankle boot with a waterproof foot. They keep you dry and warm through the cold weather months.

Our selection of men's Eastland boots has both casual and dressy styles. Men's leather ankle boots have an air of sophistication to them. Leather men's dress boots are great for special occasions like weddings, parties, and other events. But you can also wear them with a pair of jeans for an elevated, more polished every-day look.

No matter what kind of ankle boot you're looking for, Exdup has you covered!