Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
Henry | Classic Leather Boots
4.8/5 based on 1700+ reviews

Henry | Classic Leather Boots

Regular price $399.95 Sale price$109.95 Saving: $290.00
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UPDATE: After 40 years of crafting leather, we’re retiring –

Only 6 pairs left before they’re gone forever

All-Day Comfort with a Stylish Edge

The Henry - Timeless Loafers are designed for men who seek both comfort and modern style. Crafted with a breathable upper, these shoes provide excellent ventilation, keeping your feet cool and fresh throughout the day. The cushioned insole offers superior shock absorption, making them perfect for long walks, work, or casual outings.

Orthopedic Support for Healthy Foot Alignment

Featuring an ergonomic sole with arch support, these shoes help distribute pressure evenly, reducing foot strain and promoting better posture. The lightweight, flexible construction ensures a natural range of motion, while the non-slip rubber outsole provides a secure grip on various surfaces. Whether you're on the move or standing for long hours, these shoes are built for lasting comfort.

Key Features:

  • Orthopedic arch support for reduced foot fatigue
  • Breathable upper keeps feet cool and comfortable
  • Lightweight and flexible for a natural feel
  • Shock-absorbing cushioned insole for superior comfort

We offer FREE Shipping!

Depending on your location, delivery may take approximately 3-7 business days.

We carefully pack all pairs of shoes ourselves and ship it straight to your door.

Every pair of shoes comes with a lifetime craftsmanship guarantee. If you don’t love it, return it for a full refund – no questions asked.

Customers love our shoes!
Premium Crafted Materials

Premium Crafted Materials

Experience the timeless elegance and feel of leather—crafted with high-quality materials

Crafted for Timeless Style

Crafted for Timeless Style

Designed with care and built to last, for everyday wear and beyond

All-Day Comfort Fit

All-Day Comfort Fit

Ergonomic design that keeps your feet happy from your morning commute to evening plans

Sustainable by Design

Sustainable by Design

Eco-conscious materials and responsible production for a better tomorrow

Hi! We are Henry and Margaret, for 34 years, we have been lovingly crafting leather shoes, pouring our heart and soul into each pair. Every shoe tells a story, woven with care and attention to detail from the finest materials we can find. Our little workshop is where we spend our days, making sure every stitch is just right. It means the world to us that you've stopped by, and we hope these shoes bring you as much joy as they've brought us in crafting them. Thank you for being a part of this journey with us.

Lifetime Craftsmanship Guarantee

Every pair of shoes comes with a lifetime craftsmanship guarantee. If you don’t love it, return it for a full refund – no questions asked.

10.000+ Americans Love Our Craftmanship!