Horse Racing Fashion Must-Haves All Season Long

Whether you’re a Derby fascinator type gal or a polkA-dot NECKtie wearing chap, we’ve got you covered this horse racing season

Derby fashion has long been a spectacle of refinement and grandeur, tracing its roots back to the Gilded Age when Churchill Downs was imagined as America’s answer to European racetracks—equal parts elegance and excitement. 

For women, it wasn’t just about the race; it was about the reveal. From silk bustled gowns and parasols in the 1890s to the tailored suits of the 1940s, Derby Day was a sartorial showcase for the well-heeled and well-dressed. As American style evolved, so did Derby attire, with louder prints, shorter hemlines, and hats growing more elaborate with every passing decade. 

Today, the Kentucky Derby remains one of the last true bastions of fashionable pageantry, where tradition and personal flair meet under wide brims and spring skies. Lucky for you, horseracing season has just begun! Enjoy our top fashion picks, followed by calendar listings, as we follow the race for the Triple Crown, with Nashville’s Iroquois Steeplechase sprinkled in for good measure.

But First: A Few Simple Ground Rules

Rule #1: Dress for the weather

Rule #2: Show off your unique style

Rule #3: Be bold with colors and patterns

Rule #4: Test out your shoes before the race

Rule #5: Don’t forget your accessories: pocket squares, belts, bowties, gloves and hats! 

Trifecta: Classic Accessories 

For Her

Kukhta Atelier Black Lace Gloves, $37.50 at Etsy

Heliades Sun Gantlet Poika Dot UV Gloves, $150 at Heliades

Cornelia James Lara Tulle Glove with Harlequin Cuff, $331 at Cornelia James 

For Him

Laura Ashley x Tie Bar Kentucky Derby Walled Garden Green Bow Tie, $38 at Tie Bar

Bird Dog Bay Derby Season Tie, $95 at Bird Dog Bay

Favourbrook Pre-Tied Polka-Dot Silk-Jacquard Bow Tie, $105 at Mr. Porter

Superfecta: Top it off 

For Her

The Hat Girls THG8742 Hat, $590 at The Hat Girls

Magenta Winning Wager Fascinator, $40 at Darling State of Mind

For Him

SG Miller Ranch Fedora Hat - Patriotic Straw, $155 at Southern Gents

Nick Fouquet Sun Beach Straw Hat, $725 at Nick Fouquet

Pick Six: Mix and match

Race 1: Haspel Classic Seersucker Suit, $695 at Perlis

Race 2: Todd Snyder Italian Linen Double-Breasted Jacket, $698 & Pants, $298 at Todd Snyder

Race 3: Etro Floral Print Jacket, $2600 at Neiman Marcus; Bound Smart Pleat Linen Trousers, $65 at Revolve   

Race 4: Strapless Silk White & Green Floral Dress, $51 at MollyHello

Race 5: ASOS LUXE organza off the shoulder tiered mini dress in blurred floral print, $169 at ASOS

Race 6: Zimmerman Turquoise Paisley Illuminate Gown, $1750 at Tuckernuck

Bonus Pick: Inspirational Race Day Dress: Oscar de la Renta Embroidered Threadwork Mini Dress

$10,990

CALENDAR LISTINGS 2025

Kentucky Derby

Location: Churchill Downs, Louisville, Kentucky

When: First Saturday in May

Distance: 1 1/4 miles

The What: Known as "The Run for the Roses," the Kentucky Derby is the most famous horse race in the U.S. It's the first leg of the Triple Crown and is known for its long-standing traditions, including mint juleps, extravagant hats, and a rich history.

Preakness Stakes

Location: Pimlico Race Course, Baltimore, Maryland

When: The third Saturday in May (two weeks after the Kentucky Derby)

Distance: 1 3/16 miles

The What:  Preakness Stakes is the second leg of the Triple Crown, and it often features a field of the best three-year-old horses. It’s a significant event for horse racing enthusiasts. The event also has a big party vibe — think massive infield concerts and lots of tradition, including the painting of the weather vane in the winning horse’s colors.

Belmont Stakes

Location: Belmont Park, Elmont, New York

When: First Saturday in June

Distance: 1 1/2 miles

The What: The final leg of the Triple Crown, the Belmont Stakes, is known for its challenging 1 1/2-mile length. Winning the Belmont often solidifies a horse's place in history as a Triple Crown winner, which is a rare and prestigious feat.

The Haskell Invitational

Location: Monmouth Park, Oceanport, New Jersey

When: Late July or early August

Distance: 1 1/8 miles

The What: This race is a major event in the summer, drawing top horses that may have competed in the Triple Crown or are looking for a big victory to help propel their careers.

Travers Stakes

Location: Saratoga Race Course, Saratoga Springs, New York

When: Last Saturday in August

Distance: 1 1/4 miles

The What: Often referred to as the "Midsummer Derby," the Travers Stakes is one of the most prestigious races for 3-year-old horses. It has a rich history and is one of the highlights of the Saratoga Racing Season.

Woodward Stakes

Location: Saratoga Race Course, Saratoga Springs, New York

When: Early September

Distance: 1 1/8 miles

The What: The Woodward Stakes is a prestigious race for older horses, often drawing the best in the field. It's a part of the summer racing season at Saratoga.

Breeders' Cup Classic

Location: Varies (rotates among major race tracks)

When: Late October or early November

Distance: 1 1/4 miles

The What: Breeders' Cup Classic is a major international horse race and part of the Breeders' Cup World Championships. It features some of the best thoroughbreds from around the world and offers one of the largest purses in horse racing.

We can’t wait to hear your favorite fashion-related stories from this year’s horse racing season. Please DM us @palominocounty for a chance to end up in our Summer Stories.

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About the Author

Suzanne Kopulos has spent 20+ years as a celebrity stylist, fashion tastemaker, and lifestyle brand builder. For nearly a decade, she was represented by Ford Models—where her keen eye for emerging trends made her an indispensable part of Chicago’s fashion scene. With degrees in both business and law, Suzanne parlayed these skills into creative strategy; she has shaped campaigns for Neiman Marcus, BCBG, Ted Baker, Lafayette 148, goop, Ulta Beauty, Nike, QVC, Vital Proteins, Macy’s, Burberry, and Kate Somerville. As a fashion industry thought leader, she was regularly featured live on-air, contributing her “fresh takes” on ABC, CBS, NBC, FOX, and WGN.