How to Celebrate the Kentucky Derby 2021

How to Celebrate the Kentucky Derby 2021

You don’t have to live in Louisville, Kentucky to celebrate the Kentucky Derby. This fascinating race, the most famous of the three races that make up the Triple Crown, has a long history of oddly specific celebratory traditions.

For those not in the know, the Triple Crown of Thoroughbred Racing, more commonly known as the Triple Crown, is the title awarded to any horse who can win the Kentucky Derby, Preakness Stakes, and Belmont Stakes. Only 13 triple crown winners have ever achieved this feat of horse racing since 1919!

This makes announcing Derby contenders and post positions all that much more exciting for true Derby devotees.

Keep reading to figure out how you too can have a bizarre and hilariously fun Kentucky Derby celebration at home this year!


Start The Day Before The Derby, Pink Friday

Pink Friday was an unofficial tradition long before it was officially adopted by the Churchill Downs twelve years ago.

When getting ready for the Kentucky Derby Kentucky Oaks is where it’s at.

On Kentucky Oaks day, the day before the Kentucky Derby, the entire Churchill Downs racetrack is festooned with pink to draw national attention to the fight against breast and ovarian cancer.

All of the guests at the Kentucky Oaks are asked to incorporate pink into their wardrobe for the day, resulting in a blushing sea of support for breast and ovarian cancer survivors. Everywhere you look at the Churchill Downs there are pink dresses, hats, fascinators, suits, sunglasses, pocket squares, ties, socks, and stilettos!on wednesdays we wear pink mean girls amanda seyfried

Attendees can even enter the Longines Kentucky Oaks Fashion Contest, for an opportunity to win a Longines timepiece. Naturally, in 2021, this contest will be virtual, taking place on Twitter and Instagram.  Check out  #myderbyfashion on Oaks or Derby day to see this year’s crop of sharp-dressed men and fuchsia fashionistas.

Deck yourself out for the occasion with this festive fascinator or one of these bold pink bowtie and pocket square combos!

Women Tea Party Headwear Cocktail Flower Bridal Feathers Mesh Derby With Clip Headband Elegant Charming Fascinator Hat Wedding aliexpressHi-Tie Classic Silk Adult Men's Wedding Party Pink Bow Tie for Men Fashion Floral Ties Hanky Cufflinks Bow Tie Set for Men aliexpress

However, it’s not all fun and games. One of the most moving traditions of this charitable initiative is the Survivors Parade. During the parade, breast and ovarian cancer survivors march along the racetrack before the running of the Longines Kentucky Oaks begins. Of course, this year the parade will be virtual due to COVID-19 social distancing protocols.

The Kentucky Oaks charitable initiative raises funds as well as visibility and awareness. Since its inception, it has raised more than $1,000,000 for charity.

In 2021 they have partnered with the Breast Health Program at Norton Cancer Institute to help cover the costs to renovate the Norton Prevention & Wellness Mobile Prevention Center. The Center provides free screening services to underserved patients age 40 and older in Jefferson and surrounding counties. Money raised through this effort has also funded the addition of 3-D mammography technology to the mobile unit.


Kentucky Derby Hats, The True Star of the Show

Even though you just wore a crazy outfit for the Kentucky Oaks the day before, the Derby is when you really want to go all out with your wardrobe.

Of course, the infamous Kentucky Derby hats are the star of the show. This is not a time for subtle, understated elegance.

woman wearing kentucky derby hat roses bows and flamingos at churchill downs


Men have also been known to get in on the tradition. The twin spires design and Churchill Downs, in general, are iconic. For the attendees of the Kentucky Oaks, the Twin Spires are just as monumental as the Eiffel Tower!

man horse racing fan wearing kentucky derby hat twin spires churchill downs


You can really let your creativity shine and go as crazy as you like where the hats are concerned. Whether it’s an entire taffeta rose the size of a beach ball, or a flock of flamingoes with floral accents, or an exact replica of the Churchill Downs, this is one the one day a year where you can put just about anything on your head without people thinking you’ve lost your marbles.

fallon tonight kentucky derby hat pink funny har with feathers crazy fancy hat

Now, there are two ways you can go about getting Kentucky Derby hat-ready.

the first option is to buy a fairly plain big hat and customize it yourself to make something totally unique. The internet is even full of easy and fun guides to help you figure out how to hot glue or otherwise attach your ribbons and bows in place.

This hat at Shein would create a good base for your creative endeavors if you’d like to go that route.

Faux Pearl Floral Decor Straw Hat Shein Big Summer Sun hat beige

Of course, if you don’t want to engage in any extra-curricular crafting adventures there are many ready-to-wear options out there.

This voluminous number will certainly keep the sun out of your eyes while keeping everyone else’s eyes on you.

FS Pink Organza Kentucky Derby Hat For Women Wide Brim Beach Big Sun Hats Flowers Elegant Ladies Wedding Church Party Fedoras aliexpress


Bold Fashion Choices

Even if you don’t do go for a wild hat this year, an interesting suit pattern or eye-catching dress is definitely called for at this event.

Whether you’re hosting a socially distant backyard Derby Party or you’re strutting your stuff at the Churchill Downs, this is one occasion where subdued threads will make you stand out for the wrong reasons.

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For women, the tradition is knee-length form-fitting or summer dresses, often accompanied by gloves. This dress paired with these gloves makes for a cute wardrobe choice that won’t overpower your hat. If you’re forgoing the hat you may want to choose bolder threads, though.

Polka Dot Belted A-Line Dress summer dress knee lenfth sheinPolka Dot Print Gloves kentucky derby outfit matching gloves white and black fancy

For men, a light or bright colored suit, possibly in a fun print, is recommended. Pocket squares and ties are optional as you can dress your suit casually or formally to your preference. Here is one option that comes in a multitude of light colors.

New Luxury Men Wedding Suits Pink 3 Pieces Custom Groom Suit Dress Tuxedo Slim fit Jacquard Blazer Double Breasted Vest Pant Set


Drinks and Food

Last, but certainly not least, no celebration would be complete without drinks and food to keep the festivities going. There are many classic Kentucky Derby favorites you can add to your spread. The essential quality of any Derby party isn’t just lauding Derby winners but having a fun, lighthearted good time in southern style.

For food your choices may want to include:

Kentucky Hot Browns (possibly one of the most southern dishes ever, this is basically an open bacon sandwich smothered in sauce)

Kentucky Burgoo (a stew with beef, pork, and chicken and a Derby classic)

Chocolate-Bourbon Pecan Pie

For drinks we recommend:

Mint Julep (really, this drink needs no introduction, though we will say that Bulleit Kentucky Straight Bourbon Whiskey is our favorite bourbon to make this with)

Black-eyed Susan Cocktail (Fresh and citrusy, this bright yellow cocktail will keep things lively. We recommend Rhum Clement Creole Shrubb D’Orange Liqueur with this one)

Long Island Iced Tea


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