Custom Handmade Leather Chukka Boots

There’s nothing quite like slipping into a pair of boots that feel like they were made for your feet alone. Our Custom Handmade Leather Chukka Boots deliver that perfect broken-in comfort from day one, thanks to premium full-grain leather that develops a rich patina with every wear.

Handcrafted using the legendary Goodyear Welt construction, these boots feature 100% leather soles with a thin rubber lining for grip — and the best part? They can be easily resoled years down the road, so your favorite pair never has to retire.

Choose from over a dozen rich leather colors and finishes to create your signature look. We’ve included a step-by-step PDF measurement guide so you get a glove-like fit every time — just download it after placing your order. Whether you’re dressing up for the office or keeping it casual on weekends, these versatile chukka boots combine timeless style with everyday durability.

To get your own pair please place an order and download the PDF HERE.  

Custom Sizing Instructions for Your Perfect Fit

• Shoe Size
Unlike our other boot styles, please select your normal, everyday shoe size.

• Foot Tracing – Highly Recommended for Best Fit (especially if you have wide feet)

1. Place a blank sheet of paper flat against a wall on the floor.
2. Stand straight up with your heel gently touching the wall.
3. Have someone carefully trace around your entire foot with a pen.
4. On the tracing paper, draw a straight line between the widest and longest parts of your foot
5. Measure this straight line in inches or centimeters and write the measurement directly on the paper.
6. Take a clear, well-lit photo of the tracing that clearly shows both the outline and the straight-line measurement.
7. Upload the photo and your foot-width measurement in the Order Notes at checkout or message us right after ordering.

• Choose Your Leather
Click the images in the dropdown menu below to select your leather type and color.

• Choose Your Sole
Select your sole using the dropdown images.
Note: Sole images do not show the final toe shape — please refer to the main product photos for the actual boot toe style.

Production & Shipping
Your boots are handmade to order. Production typically takes 1–8 weeks depending on leather availability and current demand. Once completed, shipping takes 3–5 business days. We will notify you of any delays. Contact us if you need them expedited.

Fit Guarantee
If the boots don’t fit perfectly after we follow your measurements, we’re happy to remake a new pair at no extra charge.
Note: No returns on custom-made items once production has started.