Kingsley Riding
Boots Built for You.
Finished by Hand.
Custom tall boots, handcrafted in Portugal. Fitted in Brewster, NY — or from anywhere via Google Meet.
Designed in the Netherlands · Handcrafted in Portugal · In-Store Fittings in Brewster, NY · 300+ Leather Options
Your Custom Boot in Three Steps
Consult
Book a fitting in-store in Brewster, NY or via Google Meet. We measure your leg and walk you through every option.
Configure
Choose your leather, color, height, sole, and details using Kingsley's 3D configurator — or let us guide you.
Receive
Your boots are handcrafted in Portugal and delivered to your door in approximately 4–8 weeks.
Shop by Discipline
Dressage
Tall, elegant, and designed for the arena. Featuring Kingsley's signature curved topline and dressage-specific fit.
Hunter / Jumper
Clean lines, classic fit, built for the hunter ring and the jump course. Available with or without laces, or with foam.
MontrealEight styles. One craft.
Lexington
The classic dressage look — accessible price, Capri silhouette.
From $880
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Capri
Kingsley's flagship dressage boot — show ring ready.
From $1,215
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Orlando
Classic field boot with lace-up vamp — dressage to cross-country.
From $1,150
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Aspen
Entry-level custom boot with interchangeable tops.
From $720
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Lyon
A lightly reinforced outer shaft and soft back option for ease of break-in.
From $999
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Olbia
Premium back-zip with stitching detail and toe cap.
From $900
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Montreal
Soft buttery leather — the boot that breaks in immediately.
From $649
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Menton
Side zipper and elastic panel for maximum comfort.
From $799
View Details →Not sure where to start?
Book a fitting and we'll walk you through every style in person or via Google Meet — no pressure, just boots.
In-Stock Demo Boots
Try before you order custom. All demo boots are available now and ship from Brewster, NY.
300+ Ways to Make It Yours
Choose your leather. Your color. Your height and heel. Every pair of Kingsley boots is built to your exact measurements — and your exact vision. Use the Kingsley 3D configurator to start designing, then book a fitting with our team to finalize your order.
Open the Configurator →How to Order
Book a fitting
In-store or Google Meet. We take your measurements and review your options.
Choose your boot
Select your model, leather, color, and details in the Kingsley configurator with our guidance.
Place your order
We submit your custom order directly with Kingsley. A deposit is required.
Receive your boots
Handcrafted in Portugal and delivered in approximately 4–8 weeks.
Questions? Email us at orders@dapperhorse.com or call 845-287-0004
Book Your Fitting
Whether you're ready to order or just exploring, our fitting appointment is the best place to start. We'll measure your leg, walk you through the Kingsley collection, and help you find the perfect boot for your discipline and budget. Available in-store in Brewster, NY or via Google Meet.
Schedule Your FittingAppointments typically last 30–45 minutes. No purchase required.
Kingsley Size Guide
Kingsley boots are sized by shoe size (EU), calf circumference, and height. Use our size guide to find your starting point — we'll fine-tune everything during your fitting appointment.