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Old Money Equestrian Style Outfit Ideas for a Heritage Look

Today, we embark on a journey to the heart of equestrian style, where the rich traditions of horsemanship and the timeless elegance of heritage fashion intertwine.

As seasoned stylists with over three decades of experience outfitting gentlemen from the rolling hills of Kentucky to the prestigious riding clubs of England, we’ve developed a keen eye for the nuances that define this classic aesthetic.

So, grab your riding crop, don your finest tweed, and allow me to guide you through the hallowed halls of equestrian elegance.

This article showcased our work with Ashton, a 28-year-old equestrian enthusiast and heir to a venerable British aristocratic legacy.

Raised on the sprawling grounds of his family’s ancestral estate, Ashton was no stranger to the world of horses and the sartorial traditions that accompanied it.

However, he grappled with the challenge of infusing his equestrian attire with a modern, youthful twist.

“I want to honour the heritage of my forefathers, but I also yearn to express my own unique sense of style.”

Together, we embarked on a sartorial journey, crafting five exquisite ensembles that perfectly captured the essence of old-money style while allowing Ashton’s personality to shine through.

The impact on his confidence and performance in the saddle was nothing short of remarkable—he clinched victory in a hotly contested polo match.

He earned the admiration of his fellow riders for his impeccable taste and unparalleled horsemanship.

Now, let’s mount up and explore the five essential old-money equestrian outfits that will have you looking like a modern-day lord of the manor:

1. The Polo Match Perfection

For a high-stakes polo match, opt for a crisp white cotton polo shirt from La Martina, the Argentine brand synonymous with the sport of kings.

Pair this with a set of tailored white jeans from Polo Ralph Lauren.

These jeans feature a slim, modern fit that allows for ease of movement in the saddle.

Layer on a navy blue wool blazer from Hackett London, a brand steeped in the rich traditions of British sporting elegance.

Complete the look with a pair of chestnut brown leather riding boots from Ariat, renowned for their exceptional craftsmanship and unparalleled comfort, and a woven leather belt in a complementary tan hue from Hermes featuring the iconic H buckle.

Accessorise with tortoiseshell aviator sunglasses from Persol, adding a rakish charm to your ensemble, and a vintage Rolex Oyster Perpetual Date in stainless steel.

This timepiece perfectly embodies the spirit of old money sophistication.

2. The Country Ride Charm

Start with a brown tweed sport coat from J.Press, featuring a classic hacking pocket and a subtle windowpane check.

Layer this over a tattersall check shirt in a complementary green and blue colourway from Cordings, a British institution renowned for its country sporting attire.

Pair these with tan corduroy breeches from Hermès, celebrated for their exceptional fit and durability.

Finish the ensemble with a pair of dark brown leather field boots from Dubarry, a brand with a rich heritage in equestrian footwear, and a woven leather belt in a matching dark brown hue from J.Crew.

Accessorise with a navy blue cashmere scarf from Begg & Co., adding a touch of warmth and refined texture to your outfit, and a pair of leather riding gloves from Dents, a brand that has been crafting exceptional gloves since 1777.

3. The Dressage Elegance

Begin with a black wool tailcoat from Cavallo, a German brand renowned for its exceptional equestrian attire. Pair this with a set of white breeches from Pikeur with a high-waisted, flattering fit that adheres to the strict dress codes of the sport.

Layer a crisp white cotton shirt from Turnbull & Asser beneath your tailcoat, and add a black silk stock tie for a touch of traditional elegance.

Complete the look with a pair of black leather dressage boots from Der Dau, a brand celebrated for its bespoke craftsmanship and attention to detail, and a black velvet helmet from Charles Owen, a leader in equestrian safety and style.

Accessorise with a pair of white leather dressage gloves from Roeckl and a simple black leather belt from Hermès, allowing the timeless elegance of your outfit to take centre stage.

4. The Hunt Club Heritage

When participating in the time-honoured tradition of the fox hunt, embrace the rich hues and textures of the autumnal countryside.

Start with a red wool hunt coat from Huntsman, a Savile Row institution that has outfitted the British aristocracy for nearly two centuries.

Pair this with a set of tan breeches from Farlows featuring a comfortable, high-waisted fit that allows for ease of movement in the saddle.

Layer a tattersall check shirt in a complementary green and red colourway from Purdey beneath your hunt coat, and add a gold silk stock pin for a touch of understated elegance.

Complete the look with a pair of black leather field boots from Vogel, a German brand renowned for its exceptional craftsmanship, and a black velvet helmet from Samshield, a leader in equestrian safety and innovation.

Accessorise with a pair of tan leather riding gloves from Herm̬es and a brass hunting horn from Swaine Adeney Brigg, a symbol of your status as a member of the hunt.

5. The Equestrian Escapade

For a relaxed day of exploring the trails and fields of your estate, opt for an outfit that combines comfort and classic style. Begin with a brown waxed cotton jacket from Barbour, a brand with a rich heritage in country pursuits.

Layer this over a blue chambray shirt from Polo Ralph Lauren, adding a rugged charm to your ensemble. Pair these with a set of tan jodhpurs from Tredstep, featuring a comfortable, stretchy fit for freedom of movement in the saddle.

Finish the look with a pair of brown leather jodhpur boots from Ariat and a woven leather belt in a matching brown hue from Anderson’s.

Accessorise with a tan cotton flat cap from Lock & Co. Hatters, a brand outfitting equestrians for over three centuries, and a pair of tortoiseshell sunglasses from Oliver Peoples, adding a touch of vintage-inspired flair to your outfit.

Dos and Don’ts

To ensure you navigate the sartorial landscape of old money equestrian style, keep these essential guidelines in mind:

Do’s Don’ts
  • Invest in high-quality, natural fabrics like wool, cotton, and leather
  • Opt for a colour palette that evokes the rich hues of the countryside – deep reds, hunter greens, and earthy browns
  • Choose timeless, well-tailored silhouettes that exude a sense of refined elegance
  • Accessorise with purpose, selecting pieces that add a touch of equestrian flair to your ensemble
  • Pay meticulous attention to grooming and the finer details of your outfit
  • Avoid overly trendy or flashy garments that detract from the classic equestrian aesthetic
  • Steer clear of synthetic fabrics or garish colours that clash with the natural beauty of your surroundings
  • Don’t neglect the importance of proper fit – ill-fitting clothes can impede your performance in the saddle
  • Refrain from overt displays of brand logos or flashy designer emblems
  • Don’t overlook the significance of proper equestrian etiquette and safety – always prioritise the well-being of your horse and fellow riders

In the final analysis, mastering the art of old-money equestrian style is all about embracing the rich traditions of horsemanship while infusing your wardrobe with a touch of personal flair.

By incorporating these five essential outfit formulas and adhering to the sartorial wisdom of the do’s and don’ts, you’ll embody the spirit of refined elegance and sporting heritage, both in and out of the saddle.

Ride into Sartorial Splendor with The VOU

Gentlemen, navigating the nuanced world of old-money equestrian style can seem as daunting as taking on a challenging cross-country course, but fear not—The VOU is here to serve as your trusted style trainer.

Imagine yourself atop a majestic steed, confidently sporting an ensemble that seamlessly blends rich equestrian heritage with modern sophistication.

At The VOU, our team of seasoned style equestrians will work tirelessly to curate a bespoke capsule wardrobe that reflects your tastes and aspirations while honouring the time-honoured traditions of the equestrian world.

So, why spend another moment lost in the wilderness of fashion uncertainty?

Take the reins of your style destiny, find your unique style with The VOU’s fashion style analysis today, and prepare to take your old-money equestrian style to uncharted heights of sophistication and refinement.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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