After originating in Britain when riders raced from one church steeple to another, steeplechase made its way to the United States, where it became very popular with the Vanderbilts and duPonts. William duPont and his wife, Annie, went on to transform James Madison’s Montpelier into the home of one of the most prestigious steeplechase events in both Virginia hunt country and the U.S., now known as the Montpelier Hunt Races. Today, the races hold a special place in the hearts of Virginians and serve as a place for horse lovers to sport high fashion equestrian fashion, hats and accessories. As sponsors of the Virginia horse racing events, we’ve compiled some ideas and inspiration for What to Wear to the Steeplechase in Virginia.

Virginia Gold Cup hat, Image: © Wine & Country Life
Virginia Gold Cup, Image by © RL Johnson for Wine & Country Life
Virginia Gold Cup hat, Image: © Wine & Country Life
Virginia Gold Cup, Image: © Wine & Country Life

Horse Race Fashion for the Gals

Horse race tailgating fashion is often motivated by the event itself and can be seen in the many details of food and drink spreads, equestrian attire and hat accessories. For the gals, consider dressing in a favorite look of Kate Middleton’s—a quilted vest or coat paired with slim straight-legged pants inspired by jodhpurs tucked into leather boots. The Duchess of Cambridge wore a green tweed jacket from classic Irish brand Dubarry during her first official public appearance of 2019, when she visited with children at King Henry’s Walk in Islington Community Garden. For a more casual look, equestrian enthusiasts also often layer vests with classic white blouses or pair an upscale pair of denim with smartly chosen accessories and outer layers, creating a practical and stylish look. 

Other outfit ideas for the horse races when it is warmer weather can include a dress or skirt over equestrienne-inspired garb. Dresses with clean lines, or patterned A-line skirts paired with a solid top, will captivate eyes on the rail. Whereas, on cooler days, try opting for weightier fabrics and sturdier pieces like wool tweed jackets paired with a suede skirt. On trend is the idea of adopting brighter, collegiate color schemes inspired by brands like Vineyard Vines or Southern Tide. Or, go for a more seasonal theme, such as for autumn, with warmer, darker colors more akin to brands like Dubarry or Ralph Lauren. Although most Virginia races take place in the fall, the spring races bring brighter fashion choices with them, including Sunday best sundresses and colorful hats. 

Looking to add a statement accessory or new outfit to your wardrobe? Be sure to visit the Shops of Middleburg. The charming shops, located in the heart of Virginia hunt country, are stocked with everything the stylish equestrian enthusiast could desire. 

Horse Race Fashion for the Guys

For the guys, steeplechase fashion begins with the classics. Men should start their outfit with closet staples like collared shirts and a tailored neutral or tweed suit jacket. For a more casual option, try a fall-colored sweater with a quilted vest or the more durable pant—jeans. Another trending element guys are opting for are khaki pants or different colored dress pants. Like the ladies, feel free to let the weather influence your shoe preference. Leather boots are great for cooler and wetter weather, while dress shoes or loafers are great for warmer weather.

Horse Race Hat Inspiration

Hats for both men and women continue to be an essential part of the steeplechase tradition and, today, are the most prominent accessory and fashion focal point for attendees. Hat pageantry has become so engrained in the culture of steeplechase that many races like the Virginia Gold Cup and Montpelier Hunt Race have “Who Wore It Best” competitions. Beyond looking stylish and potentially securing your first-place prize in a contest, hats also provide protection from the sun and can help secure an elegant updo from the wind.

Embrace the spirit of the occasion and create a work of art with eye-catching arrangements of flowers, feathers, ribbon, equestrian accents and more. 

To elevate and personalize an understated hat, consider adding a sophisticated scarf or pin. Or, embrace the spirit of the occasion and create a work of art with eye-catching arrangements of flowers, feathers, ribbon, equestrian accents and more. You’ll be surprised at how a subtle fascinator can add a touch of elegance. 

Gentlemen also enjoy flaunting their headwear fashion in top hats, round bowlers, natty straw boaters or a classic tweed newsboy hat with visor. Adding a belt or a single feather to a hat can give it an extra festive touch. Not to be outdone, some men even join in on the extravagant feather and flower frenzy by decking out their hats in their own favorites.

Equestrian Accessory Ideas

For all attendees, it’s tradition, and fashion-forward, to showcase equestrian accessories and motifs, such as riding boots, horse bits and horseshoe embellishments. No matter how small the touch or detail is, you can use it to customize your look and have you fitting in to the scene.

When it comes race day footwear, always choose comfy, closed-toe shoes. Boots that are sturdy, durable and fashionable are ideal for a day at the steeplechase. The Dubarry Galway is the unofficial saddle boot of Virginia Hunt Country. Its genuine and authentic leather is tailored for everything—from any everyday stroll in the country to an afternoon ride. It is an equestrian staple that keeps feet dry in the midst of tall grass with no need to worry about mud. Perhaps the best part is that you just need rinse them off with the water hose after a day out in the breathtaking countryside.

When it comes to steeplechase jewelry, gold is king. Statement jewelry is a great way to incorporate equestrian-themed items into your outfit. For a different but still chic adornment, try substituting a necklace for an elegant race-inspired brooch. To get an authentic Virginia steeplechase piece, shop local. Artisans like Elizabeth Locke incorporate race day staples into her work. You can also find equestrian-themed jewelry and elegant steeplechase fashion pieces at the Wine & Country Shop


Foxfield Races Fall 2022


A bag or purse is an extension of your wardrobe that is an opportunity to be just as stylish as it is useful. No matter whether you are seeking style over function, all bag styles make great statement pieces. A clutch can match your feminine ensemble, while a small personal handbag or backpack can be helpful for toting essential items. The Hermès birkin purse is an iconic leather bag that can often be spotted on race days. Its smooth leather surface and rectangular shape is the perfect combination of luxury and practicality. 

We must not forget the accessories for the men, as they are just as important in completing an equestrian-infused look. Suspenders and bow ties are dapper statement pieces that are excellent ways to show some flair. Choose ties with bright colors, patterns or even school-inspired prints, and don’t be hesitant in sporting personalized pocket squares. At the races, leather accessories rule for men, and you can often spot rustic cigar carriers or bespoke flasks. Fill it up with a favorite Virginia spirit and you’re ready for the races!

Practical Fashion Tips for the Steeplechase

Before heading out, don’t forget a few other must haves. Make sure to pack hand sanitizer, tissues, lipstick and a water bottle to keep you fueled and feeling your best. Since the races are outdoors, don’t forget sunscreen and bug repellent. Check the weather forecast before heading to the steeplechase to accommodate for any rain or inclement weather that may call for outfit adjustments or for bringing along an umbrella.

In terms of What to Wear to the Steeplechase, hunt country fashion is not to be missed. In all of your elegantly equestrian fashion choices, you will be feeling like a steeplechase star. Who knows, you might even find yourself sporting the top look at the races. We hope you feel inspired to start planning your steeplechase ensemble for the upcoming horse race season. Read our comprehensive guides for The Montpelier Hunt RacesFoxfield Races and International Gold Cup online. You can also find expert tips on Decorating your Steeplechase Tailgate, Easy Tailgate Dish Ideas, Styling the Ultimate Steeplechase Tailgate and Dessert Ideas in our Tailgating section. For tailgating supplies, equestrian inspiration and elegant servingware, visit The Wine & Country Shop online or in person in Ivy.  ~


Tailgate Etiquette: Tips for Being a Great Guest

Want a cheatsheet for how to be the ultimate guest at your next tailgate? Download our Wine & Country Guest Guide to the Steeplechase Races by clicking the image below.

MANDY REYNOLDS, a former press liaison for the Edinburgh International Festival, has a master’s in art and history and enjoys local culture especially our delicious farm-to-table cuisine.

R. L. JOHNSON is our co-publisher and creative director, Robin Johnson Bethke, who began her career as a professional photographer in Los Angeles before moving into graphic design and art direction when she relocated to Charlottesville in 1994. As our company’s co-founder and visionary, she enjoys all aspects of the publishing process from story conception to graphic design to photography. Her work is often seen in many of our publications.

Wine & Country celebrates elevated living in Virginia Wine Country. Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The annual Wine & Country Wedding Planner is an art book of elegant Virginia weddings. The brand includes the Wine & Country Shop in Ivy, Va. It is a beautiful lifestyle boutique that brings the pages of the magazines to life. Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media also provides branding, web design and PR services for the wine industry.