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Men's Leather Side-Zip Ankle Boots Cushioned Footbed - Brown
Men's Leather Side-Zip Ankle Boots Cushioned Footbed - Blue
Men's Leather Side-Zip Ankle Boots Cushioned Footbed - Black
Men's Leather Side-Zip Ankle Boots Cushioned Footbed - White
Men's Leather Side-Zip Ankle Boots Cushioned Footbed - Khaki

Henry | Men's Leather Side-Zip Ankle Boots Cushioned Footbed

Regular price $120.00 Sale price$59.95 Save 50%
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Over 165 customers say this style fits true to size for them.

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WINTER SALE
50% OFF EVERYTHING
Now is the time to shop your favorite winter dresses at irresistible prices. While stocks last!

Men's Leather Side-Zip Ankle Boots Cushioned Footbed are your go-to choice for long workdays, errands, and casual outings where comfort and ease matter. Built with a cushioned footbed, a side zipper for quick on-and-off wear, and a rounded toe with room for thicker socks, these mens zipper ankle boots are crafted for men who stay on their feet.

Why You'll Love It

  • Cushioned Footbed: A built-in cushioned layer absorbs impact and keeps feet comfortable through long hours of standing or walking.
  • Side-Zip Entry: The inner side zipper makes getting in and out effortless, no lacing needed every morning.
  • Roomy Rounded Toe: The rounded toe box leaves space across the front, so you can wear thicker socks comfortably in cooler weather.

Perfect For

Pair them with straight jeans for a relaxed weekend look, or wear them with chinos for a smarter casual day at the office. They slip easily under a long coat in winter and work just as well on a weekend city walk or a full day on your feet at work.

Care Instructions

  • Wipe clean with a soft, damp cloth.
  • Allow to air-dry away from direct heat or sunlight.
  • Store upright with a shoe tree to maintain shape.
  • Re-treat the surface periodically to keep the upper looking fresh.

Frequently Asked Questions

Does the side zipper run along the inner or outer side of the boot?
The zipper runs along the inner side of the boot, making it easy to slip on and off without bending the upper.

Is there enough room in the toe box for thicker winter socks?
Yes, the rounded toe is designed with extra room across the front specifically to accommodate thicker socks.

How should I style these boots?
They pair well with straight jeans or chinos for a smart casual look, and work great layered under a long coat during colder months.

Men's Shoe Size Chart

US Size Foot Length (in)
US 4 8.75
US 4.5 9.0
US 5 9.1
US 5.5 9.3
US 6 9.5
US 6.5 9.6
US 7 9.75
US 7.5 10.0
US 8 10.1
US 8.5 10.3
US 9 10.5
US 9.5 10.6
US 10 10.75
US 10.5 11.0
US 11 11.1
US 11.5 11.3
US 12 11.5

If you're unsure between sizes, always go one size up. This ensures maximum comfort while maintaining a great fit.

Not the right fit? You can request a return within 30 days of delivery, for any reason. See our Refund Policy for all details.

Every order ships free within the United States, with tracking included. Orders are processed within 1–3 business days and delivered within 6–10 business days after shipping.

30-Day Return Promise

We love our pieces and we’re confident you will too. That’s why every order comes with our 30-day return promise: if something isn’t quite right, you can request a return within 30 days of delivery, for any reason.

Read our Refund Policy

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30-Day Returns

Not the right fit? You can request a return within 30 days of delivery.

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Henry | Men's Leather Side-Zip Ankle Boots Cushioned Footbed