I N C E P T I O N A I
  2. Sports outdoors
  3. Equestrian
  4. Horse saddles
  5. English saddles
  6. English sidesaddle saddles

Top 5 English Sidesaddle Horse Saddles in Canada for 2025: Certified Guide to Traditional and Modern Models for Comfort, Safety, and Show Performance

Published on Monday, August 25, 2025

Traditional sideways-riding saddles with fixed or adjustable leaping horns and pillion options designed for equitation and show sidesaddle remain a niche but growing category in Canada. Riders choose English sidesaddles for a mix of historical style and modern functionality: they want a saddle that honors classic lines for shows and parades while delivering contemporary tree designs, improved safety features, and better fit for both horse and rider. Canadian buyers prioritize saddles that perform in variable climates, offer durable materials or low-maintenance synthetic options, and can be custom-fitted to local horse types. Across urban competition circuits and rural breeding farms, preferences gravitate toward models that balance authentic appearance with pressure-distributing trees, secure leaping horns, and pillion choices that make transitions and mounted work safer and more comfortable.

Quick Menu

1. Best Classic Reproduction

2. Best Victorian Style

3. Best Accessible Modern

4. Best Competition Champion

5. Best Contemporary Elegance

1
BEST CLASSIC REPRODUCTION

Mayhew Ladies Side Saddle

Mayhew

Mayhew Ladies Side Saddle is a best-in-class choice for traditional English sidesaddle riders thanks to its hand-crafted leatherwork, balanced tree and accessible price point that makes it a cost-effective entry into sidesaddle riding compared with pricier boutique makers. Its technical strengths are a proven tree design and affordable custom options, giving riders a reliable blend of historical style and modern fit versus the more specialized Victorian or high-performance show saddles in this list.

4
★★★★☆

  • Timeless Mayhew charm

  • Supportive rider seat

  • Timeless Mayhew charm

  • Supportive rider seat

Review Summary

78%

"Buyers generally appreciate the Mayhew Ladies Side Saddle for its traditional styling and solid build for occasional use; several owners note the leather and fit often require professional servicing and it's less comfortable for everyday riding."

  • Rugged English leather

  • Traditional cut-and-sew leather construction for a period-correct appearance

  • Rugged English leather

  • Traditional cut-and-sew leather construction for a period-correct appearance

Skill Development & Mastery

Recreational Enjoyment

Mayhew Ladies Side Saddle is a best-in-class choice for traditional English sidesaddle riders thanks to its hand-crafted leatherwork, balanced tree and accessible price point that makes it a cost-effective entry into sidesaddle riding compared with pricier boutique makers. Its technical strengths are a proven tree design and affordable custom options, giving riders a reliable blend of historical style and modern fit versus the more specialized Victorian or high-performance show saddles in this list.

  • Timeless Mayhew charm

  • Supportive rider seat

  • Rugged English leather

  • Traditional cut-and-sew leather construction for a period-correct appearance

  • Fixed padded seat with leaping head for rider security and elegant posture

  • Timeless Mayhew charm

  • Supportive rider seat

  • Rugged English leather

  • Traditional cut-and-sew leather construction for a period-correct appearance

  • Fixed padded seat with leaping head for rider security and elegant posture

Order Now

$2,000-4,500 CAD

2
BEST VICTORIAN STYLE

Owen Dare-Lynch Victorian Side Saddle

Owen Dare-Lynch

The Owen Dare-Lynch Victorian Side Saddle leads the market for historical authenticity and period-correct construction, making it the preferred option for reenactment and classical hunters who need an authentic English sidesaddle silhouette. Though generally priced above everyday models like the Whippy Original, its traditional hardwood or reinforced tree and meticulous stitching offer longevity and collector value that justify the premium for riders prioritizing authenticity over low-maintenance modern features.

4.2
★★★★☆

  • Ornate Victorian flair

  • Museum-grade detailing

  • Ornate Victorian flair

  • Museum-grade detailing

Review Summary

81%

"Owners praise the Owen Dare-Lynch Victorian Side Saddle for authentic Victorian styling and handcraftsmanship, but many report it is heavy, expensive and frequently needs custom fitting to be truly comfortable."

  • Tea-room approved

  • Handcrafted British leatherwork replicating authentic Victorian-era design

  • Tea-room approved

  • Handcrafted British leatherwork replicating authentic Victorian-era design

Recreational Enjoyment

Skill Development & Mastery

The Owen Dare-Lynch Victorian Side Saddle leads the market for historical authenticity and period-correct construction, making it the preferred option for reenactment and classical hunters who need an authentic English sidesaddle silhouette. Though generally priced above everyday models like the Whippy Original, its traditional hardwood or reinforced tree and meticulous stitching offer longevity and collector value that justify the premium for riders prioritizing authenticity over low-maintenance modern features.

  • Ornate Victorian flair

  • Museum-grade detailing

  • Tea-room approved

  • Handcrafted British leatherwork replicating authentic Victorian-era design

  • Deep, supportive seat and knee rolls that enhance stability and control

  • Ornate Victorian flair

  • Museum-grade detailing

  • Tea-room approved

  • Handcrafted British leatherwork replicating authentic Victorian-era design

  • Deep, supportive seat and knee rolls that enhance stability and control

Order Now

$3,500-6,500 CAD

3
BEST ACCESSIBLE MODERN

Whippy Original English Side Saddle

Whippy

The Whippy Original English Side Saddle is a market leader for everyday sidesaddle use, prized for a modernized interpretation of classic lines that delivers easier mounting and predictable balance for schooling and hacking riders. Financially it occupies a sensible mid-range between budget-conscious Mayhew options and the high-end Victorian or show saddles, while technically it often offers a lighter tree and adjustable flaps that reduce long-term fitting costs.

4.6
★★★★☆

  • Original Whippy design

  • Featherlight handling

  • Original Whippy design

  • Featherlight handling

Review Summary

90%

"Riders commonly commend the Whippy Original English Side Saddle for its modern shaping, light weight and reliable balance, with consistent build quality and helpful aftercare; a minority mention longer lead times for custom orders."

  • Modern comfort tweak

  • Lightweight modern construction designed for everyday schooling and comfort

  • Modern comfort tweak

  • Lightweight modern construction designed for everyday schooling and comfort

Skill Development & Mastery

Recreational Enjoyment

Enhanced Physical Well-Being

The Whippy Original English Side Saddle is a market leader for everyday sidesaddle use, prized for a modernized interpretation of classic lines that delivers easier mounting and predictable balance for schooling and hacking riders. Financially it occupies a sensible mid-range between budget-conscious Mayhew options and the high-end Victorian or show saddles, while technically it often offers a lighter tree and adjustable flaps that reduce long-term fitting costs.

  • Original Whippy design

  • Featherlight handling

  • Modern comfort tweak

  • Lightweight modern construction designed for everyday schooling and comfort

  • Balanced tree and adjustable fittings to suit a wide range of horses

  • Original Whippy design

  • Featherlight handling

  • Modern comfort tweak

  • Lightweight modern construction designed for everyday schooling and comfort

  • Balanced tree and adjustable fittings to suit a wide range of horses

Order Now

$1,800-3,000 CAD

4
BEST COMPETITION CHAMPION

Martin & Martin Champion Side Saddle

Martin & Martin

The Martin & Martin Champion Side Saddle is favored in competitive English sidesaddle circles for its refined balance, reinforced points for jumping and show-oriented features that give riders a performance edge in the ring. Its higher upfront cost is offset by professional-grade materials and consistent fit that tend to preserve resale value better than many general-purpose saddles on this list, making it a solid investment for serious competitors.

4.8
★★★★☆

  • Competition-ready build

  • Precision-balanced seat

  • Competition-ready build

  • Precision-balanced seat

Review Summary

95%

"The Martin & Martin Champion Side Saddle is widely regarded as a top professional saddle for fit, durability and refined balance; buyers consistently praise its craftsmanship and long-term comfort despite a premium price."

  • Winner's silhouette

  • Competition-oriented build with reinforced tree and performance leather

  • Winner's silhouette

  • Competition-oriented build with reinforced tree and performance leather

Skill Development & Mastery

Enhanced Physical Well-Being

The Martin & Martin Champion Side Saddle is favored in competitive English sidesaddle circles for its refined balance, reinforced points for jumping and show-oriented features that give riders a performance edge in the ring. Its higher upfront cost is offset by professional-grade materials and consistent fit that tend to preserve resale value better than many general-purpose saddles on this list, making it a solid investment for serious competitors.

  • Competition-ready build

  • Precision-balanced seat

  • Winner's silhouette

  • Competition-oriented build with reinforced tree and performance leather

  • Forward-cut seat and strong cantle for secure position in show work

  • Competition-ready build

  • Precision-balanced seat

  • Winner's silhouette

  • Competition-oriented build with reinforced tree and performance leather

  • Forward-cut seat and strong cantle for secure position in show work

Order Now

$3,000-6,000 CAD

5
BEST CONTEMPORARY ELEGANCE

Lillian Whippy Modern Side Saddle

Lillian Whippy

The Lillian Whippy Modern Side Saddle represents the contemporary premium option, blending Whippy heritage with modern safety features and lightweight materials tailored to English sidesaddle riding. Typically commanding a premium over the Original model, it delivers reduced maintenance, advanced ergonomics and often factory-backed fitting support, positioning it as the go-to for riders seeking the latest technical refinements.

4.7
★★★★☆

  • Contemporary Lillian style

  • Ergonomic rider support

  • Contemporary Lillian style

  • Ergonomic rider support

Review Summary

92%

"The Lillian Whippy Modern Side Saddle is highly rated for contemporary comfort and adjustable fitting, with owners citing excellent customer service and strong rideability, though bespoke builds can have extended lead times."

  • City-chic flair

  • Modern Whippy-inspired design combining classic lines with updated comfort

  • City-chic flair

  • Modern Whippy-inspired design combining classic lines with updated comfort

Enhanced Physical Well-Being

Skill Development & Mastery

Recreational Enjoyment

The Lillian Whippy Modern Side Saddle represents the contemporary premium option, blending Whippy heritage with modern safety features and lightweight materials tailored to English sidesaddle riding. Typically commanding a premium over the Original model, it delivers reduced maintenance, advanced ergonomics and often factory-backed fitting support, positioning it as the go-to for riders seeking the latest technical refinements.

  • Contemporary Lillian style

  • Ergonomic rider support

  • City-chic flair

  • Modern Whippy-inspired design combining classic lines with updated comfort

  • Ergonomic seat and adjustable straps to optimise rider fit and balance

  • Contemporary Lillian style

  • Ergonomic rider support

  • City-chic flair

  • Modern Whippy-inspired design combining classic lines with updated comfort

  • Ergonomic seat and adjustable straps to optimise rider fit and balance

Order Now

$2,200-4,000 CAD

What Research Says About Sidesaddle Fit, Safety, and Horse Comfort

Scientific work in equine biomechanics and saddle fitting supports the idea that properly designed sidesaddles can reduce peak pressure points, improve rider stability, and protect horse back health when fitted correctly. Research using pressure-mapping technology, motion-analysis, and veterinary assessments—published in equine science journals and produced by North American veterinary schools—shows that tree shape, panel distribution, and rider position are key factors for minimizing back strain. For beginners, this means selecting a modern sidesaddle that incorporates updated tree geometry and vetted panel materials is likely to promote long-term soundness and better performance in ring work and schooling.

Pressure mapping studies show modern tree designs spread load more evenly than poorly fitting traditional trees, reducing localized pressure peaks on the horse's back.

Biomechanics research indicates that adjustable leaping horns and secure seat design help the rider maintain balance without excessive compensatory movement that could stress the horse.

Veterinary reviews emphasize that regular professional saddle fitting and periodic checks are critical to sustain horse comfort and avoid lameness associated with poor fit.

Material science advances (lighter synthetic panels, breathable flocking) contribute to rider comfort and easier maintenance in Canada’s seasonal climate.

Education and certified saddle fitters improve outcomes; riders who work with a qualified fitter see better performance and longer service life from their saddles.

In Canada for 2025 the English sidesaddle market highlights both faithful recreations and modern reinterpretations. The Mayhew Ladies Side Saddle and the Owen Dare-Lynch Victorian Side Saddle are strong choices for riders seeking classic show lines, while the Whippy Original English Side Saddle and the Martin & Martin Champion Side Saddle offer established performance and craftsmanship. For most Canadian riders looking to blend historical styling with contemporary safety and fit, the Lillian Whippy Modern Side Saddle is often the best overall choice. We hope you found what you were looking for — if not, refine or expand your search using the site search to compare fit, tree type, and local fitter options.

Discover More
  • English Dressage Horse Saddles
  • English Jumping Horse Saddles
  • English Eventing Horse Saddles
  • English All Purpose Horse Saddles
  • English Racing Horse Saddles
  • English Polo Horse Saddles
  • English Show Hunter Horse Saddles

Copyright © 2025 InceptionAi Inc.

Trademark Policy

Articles

About Us

Contact Us

Careers

Sitemap