Time to Grab Your Fanciest Hats and Cheer for the Fastest Horses at the 151st Kentucky Derby

Compiled by Grayling Holmes

Grab your hats & cheer for your horses for Kentucky Derby Day, this year held on Saturday, May 3rd.  The Derby is known for its sea of hats. Hats symbolize elegance and refinement from the early days. Hats are considered a sign of good luck, so the tradition has endured to this day. From fascinators, to feathers and floras, to more sculptural pieces, big hats are the order of the day.

Although the more noticeable and flamboyant hats are worn by women, men also wear hats, mostly Fedoras and bowlers.

Here’s a little history on the race…

According to Wikipedia:

Held annually on the first Saturday in May, the Derby is the first leg of the Triple Crown. It is preceded by the two-week-long Kentucky Derby Festival. The race is known as "The Run for the Roses", as the winning horse is draped in a blanket of roses. Lasting approximately two minutes, the Derby has been alternately called "The Most Exciting Two Minutes in Sports", "The Fastest Two Minutes in Sports", or "The Greatest Two Minutes in Sports", coined by Churchill Downs president Matt Winn. At least two of these descriptions are thought to be derived from the words of sportswriter Grantland Rice, when in 1935 he said "Those two minutes and a second or so of derby running carry more emotional thrills, per second, than anything sport can show."

If you can’t hop a flight to Louisville, and don’t want to sit on your couch to watch on TV, here are some ways to get out and about to Watch Parties in St. Louis to enjoy the 151st Run for the Roses and sport your finest Derby hat.

Four Seasons Kentucky Derby Watch Party

Luxury. Fashion. Thrill. Elegance. 

Join them for a high-society Derby experience like no other at the prestigious Four Seasons Hotel. Immerse yourself in an afternoon of exquisite dining, signature cocktails, a high-fashion runway shows, and thrilling race-day entertainment.

 Event Highlights

Runway Fashion Shows – Featuring exclusive couture by The Vault Luxury Resale and Noble Luxury Brands

Custom Derby Hat Showcase – Featuring award-winning milliner, Dianne Isbell.

Award-winning milliner, Dianne Isbell, and friends at the Four Seasons St. Louis.

 Welcome Drink – Savor the Angel’s Envy Mint Julep, a classic Kentucky Derby drink, complimentary with GA and VIP tickets upon your arrival.

 Best Dressed Contest Including Prizes

  • Best Dressed Gentleman- Gift certificate for bespoke clothing at Noble Luxury Brands

  • Best Dressed Lady- Gift certificate for The Vault Luxury Resale

  • Best Hat Award- Work with Dianne Isbell to design a chic & unique derby hat

Ladies enjoy showing off their finest hats at the Four Seasons St. Louis Kentucky Derby Party.

Horse Name Draw & Raffle Lounge – Every guest who purchases a ticket to the event will receive one complimentary raffle ticket. Additional raffle tickets will be available for purchase for more in chances to win.

Gourmet Food & Signature Cocktails – Indulge in a handcrafted Derby Day menu.

4 Hands + Peacemaker Kirkwood Derby Bash

Saddle up, STL, and join 4 Hands + Peacemaker Kirkwood at 157 W. Argonne for Derby Day, a bash full of big hats, bold drinks and beautiful oysters! 

Prizes

They’ll award prizes for best dressed and best hat,

Drinks

Pour 4 Hands, 1220 Spirits and Withered Oak twists on classic derby drinks and offer a raw bar featuring freshly shucked oysters from the Peacemaker Lobster & Crab Co. kitchen.

Live Music

Because this party needs more than 120 seconds of excitement, they’ll have live music from the Mike Murano trio to keep things grooving!

All ages are welcome, but anyone under the age of 18 must be supervised by an adult. They do not take reservations or hold tables. All seating is open and first come first serve. 

Westport Plaza Derby Day

Westport Plaza in St. Louis will be hosting a Kentucky Derby watch party on Saturday, May 3rd, from 1 PM to 6 PM. The event, presented by Four Roses Bourbon, will feature a big screen showing of "The Run for the Roses," along with live music, a full bar including Mint Juleps, and potentially hat contests and giveaways.

Gateway City Derby

Join the Epsilon Lambda Charitable Foundation and the Metro East. St. Louis Community Initiative for the Gateway City Derby Party Experience hosted by the distinguished men of Alpha Phi Alpha!

This event will take place at the spectacular Post Building, featuring a dynamic venue to enjoy your favorite cocktail. The Gateway City Derby is hosted by the St. Louis Alphas (Epsilon Lambda Chapter - St. Louis, MO) and the East St. Louis Alphas (Delta Epsilon Lambda - East St. Louis, IL). We invite all derby party fans to get dressed up and come experience the pageantry and elegance of the Derby event, and party to great music from one of the best DJs in the area.

So get your hats, bow ties, and finest derby outfit and get ready to experience the Gateway City Derby in the Heart of Downtown!

Visit GatewayCityDerby.com, or contact us at GatewayCityDerby@gmail.com for more information.

Diversity Golf and H&B Supplies Derby Day

Join them for an unforgettable Derby Day experience filled with games, giveaways, networking, and good times! Dress in your finest Derby attire and celebrate with:

Exciting Activities & Prizes

  • Silent Auction featuring baskets & excursions

  • Raffle Items & Betting Boards

  • Cognac Tasting & Wine/Liquor Pull

  • Cash Bar & Delicious Food/Desserts

  • Free Gifts for Attendees

Derby Fashion Contests

  • Best Dressed Gentleman

  • Best Ladies’ Hat

  • Best Dressed Couple

Enjoy an afternoon of Southern charm, thrilling races, and festive fun while connecting with fellow guests in an elegant setting.

Ticket price includes free gifts, two drinks, and food.

Purchase Tickets Now: handbsupplies.org

Wear your best Derby outfit & celebrate in style!

Sat, 03 May at 02:00 pm to 07:00 pm  1043 South Brentwood Boulevard, 17th floor, St. Louis, MO 63117