Kingsley
Orlando
All the structure, all the grip
— built for every type of rider.
The Orlando is the boot for riders who need their footwear to perform — not just look good. A laced front vamp with eye hooks gives it that classic field boot silhouette, while the choice between a back zipper (01) or front inside zipper (02) means you get the fit and function you prefer. Tough enough for cross-country, polished enough for the dressage ring.
Built to your specifications.
Every Kingsley boot is handcrafted in Portugal. Configure online — or let our team guide you through every option in a fitting.
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01Sub-style: 01 (back zipper) or 02 (front inside zipper).
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02Lacing: Eye hook lacing detail across the vamp.
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03Leather: Leather color and finish options.
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04Sizing: Custom calf and ankle sizing for a true fit.
Real Orlandos, in stock at Dapper Horse.
Try our demo boots at our Brewster store — get fitted and see your customization options come to life.
Your Orlando in four steps.
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Step 01
Book a fitting
In-store in Brewster, NY or via Google Meet.
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Step 02
Get measured
We fit your leg and walk you through every option for the Orlando.
Not sure of your size? Kingsley Size Guide →
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Step 03
Configure & order
Finalize your boot using Kingsley's 3D configurator — online or with our guidance.
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Step 04
Receive your boots
Handcrafted in Portugal and delivered to your door in approximately 4–8 weeks.