The Boot Collection
Every Step,
A Masterpiece
Polo boots, long riding boots, short boots — each pair handcrafted from premium full-grain leather by artisans with generations of expertise.
Heritage & Craft
Boots Built
to Last a Lifetime
Since 1987, Chicago Leather Co. has been the trusted choice of polo players, equestrians, and discerning gentlemen worldwide. Every boot that leaves our atelier is a product of obsessive attention to detail — from the careful selection of the hide to the final hand-stitched welt.
Browse by Type
Find Your
Perfect Boot
The field-proven choice of professional polo players — engineered for performance, refined for elegance.
Shop Polo BootsTall, commanding, and impeccably fitted. The definitive riding boot in full-grain leather.
Shop Long BootsVersatile, refined ankle and paddock boots that move seamlessly from the stable to the street.
Shop Short BootsYour exact measurements, chosen leather, and personal monogram. One-of-a-kind craftsmanship.
Start Custom OrderReinforced soles, grip panels and sport-grade stitching — built for the most demanding conditions.
Shop Sport BootsRefined everyday leather boots — Chelsea, chukka, and derby styles that pair luxury with modern comfort.
Shop Casual BootsWhy Chicago Leather Boots
The Difference
is in the Detail
Full-Grain Leather
Only the finest top layer of the hide is used — the strongest, most beautiful, most durable part of the skin.
Lifetime Warranty
Every boot is built to outlast trends and seasons. Our craftsmanship warranty covers structural defects for life.
Secure & Discreet
SSL-encrypted checkout, discrete packaging, and insured worldwide delivery on every order placed.
Free Global Shipping
Complimentary insured shipping on all orders over $200, delivered to your door in a signature keepsake box.
Bespoke Atelier
Your Boot,
Your Way
Consultation & Specification
Choose your leather grade, colour, height, toe shape, sole type, and any personal monogram or embossing.
Precision Measurement
We take 14 individual measurements of your foot and calf to ensure an exact anatomical fit — not a size approximation.
Hand-Lasted Construction
Our master cobblers last each boot by hand, stitch the welt, and finish with our signature sole and heel.
Final Inspection & Delivery
Every pair undergoes a meticulous 28-point quality check before being packaged in our presentation box and shipped worldwide.
Material Selection
Choose Your Leather
Midnight Black
Classic, commanding, timeless. Full-grain calf leather.
Dark Havana
Rich espresso brown with deep natural grain character.
Sahara Tan
Warm, natural tones that deepen beautifully with age and wear.
Cognac
Luminous amber-red tones, beloved by polo professionals.
Oxblood
Deep burgundy-red with aristocratic presence and character.
Midnight Navy
Rare, distinguished navy-dyed leather for the bold collector.
Forest Green
Earthy deep green — a signature colour for the country sportsman.
From Our Clients
Trusted by Champions
The polo boots are the finest I have ever worn. The fit after break-in is like a second skin — I haven't used any other brand since my first pair three years ago.
I ordered long riding boots with a custom calf circumference. The precision of fit is something I've never experienced from any ready-to-wear brand. Absolutely worth every penny.
We outfitted our entire polo team with Chicago Leather boots this season. The consistency of quality across every pair was remarkable. They are now our permanent supplier.
Ready to Begin?
Your Boots,
Made by Hand
Every great pair of boots begins with a conversation. Tell us what you need — and our master artisans will create something that will outlast generations.