@usweekly #ad @Madison LeCroy’s ultimate Derby Party hosting guide is here, just in time to prep for this year’s Kentucky Derby 🌹 #WoodfordReserve cocktails, festive fashion, party traditions and more at the link in bio! 21+ #drinkresponsibly
If there’s one event on the calendar that practically begs you to go all out, it’s the Kentucky Derby. This year, Southern Charm’s Madison LeCroy is serving up a Triple Crown of hosting tips –– with Woodford Reserve at the center –– for the ultimate at-home Derby celebration.
In an exclusive Hosting With Us video, the Charleston-based star — known for her effortless Southern style and knack for entertaining — opens the doors to her home and breaks down everything you need to throw a Derby Day party that feels equal parts elevated and easy. From signature cocktails to standout style and crowd-pleasing traditions, Madison proves you don’t need to be at Churchill Downs to celebrate like you’re trackside.
A Perfect Derby Day Starts With the Bar
“Build the decor around the bar,” Madison says — and for good reason. It’s the natural gathering place and visual centerpiece. Get that right and everything else falls into place.
Style it with fresh roses (a nod to the Derby’s signature flower), mint sprigs and subtle gold accents for a setup that looks stunning without feeling overdone.
Her must-have? A bottle of Woodford Reserve — the official bourbon of the Kentucky Derby — plus two essential cocktails: the refreshing Woodford Spire and the iconic Mint Julep.
Photo Credit: Faith Pratt
The Cocktails You Need for Kentucky Derby Day
Madison walks us through two essential Derby Day drinks, starting with the one you might not know yet.
The Woodford Spire — named after the iconic Twin Spires at Churchill Downs — is her go-to crowd-pleaser. “If you haven’t had a Woodford Spire, you’re missing out,” she says. The recipe is simple and batch-friendly: 1.5 oz Woodford Reserve, 2 oz lemonade and 1 oz cranberry juice, shaken, served over ice and garnished with a lemon twist. It’s bright, refreshing and always a crowd favorite.
Photo Credit: Faith Pratt
Then there’s the Classic Mint Julep — the non-negotiable. Made with 2 oz Woodford Reserve, a half-ounce of Woodford Reserve Mint Julep cocktail syrup and fresh muddled mint over crushed ice, it’s the most iconic sip in sports for a reason.
Photo Credit: Faith Pratt
Dress the Part For Your Kentucky Derby Party
When it comes to Derby Day fashion, Madison’s motto is clear: more is more. Think statement dresses, bold fascinators and accessories that turn heads the second you walk in.
“Whether you’re cheering at Churchill Downs or watching at home with your girls, the Kentucky Derby is one of the only days you can be this extra — and it’s encouraged,” Madison says.
Her look is peak Derby: a statement dress, a bold fascinator, and earrings and heels to tie it all together. The 2026 Derby fashion mood is all about vibrant color, playful prints and textures that make a statement — think electric blues, bright pinks and citrus tones paired with a fascinator that steals the room.
Photo Credit: Faith Pratt
The Guys Get a Moment on Derby Day, Too
Madison doesn’t let the men off the hook. “I think all you ladies have a handle on Derby style,” she says, “but for the men out there — this is the moment for you fellas to really show off your style.”
Cue husband Brett Randle stepping into frame. Madison puts the finishing touches on his look — a pastel blazer, pocket square, loafers, sunglasses and a hat — before delivering the verdict: “Now that’s a first-place look.” The two toast their Woodford Reserve cocktails, and honestly? It’s the Derby Day couple energy we all need.
The Derby Day Party Moments That Bring People Together
Once the drinks are flowing and the outfits are on full display, Madison turns her focus to what really makes a Derby party unforgettable: the shared moments.
Her go-to traditions are simple but effective. A way to get everyone in on the Derby Day action.
Friendly Derby Betting Pool
Madison keeps it simple and approachable: guests pick horses before the race, and the winner takes home a commemorative bottle of Woodford Reserve — the official bourbon of the Kentucky Derby — plus bragging rights for the entire year. “Nothing crazy,” she says. “Just enough to make it interesting.”
Derby Day Best Hat / Best Dressed
“I always do a little ‘best hat’ or ‘best dressed’ moment — because honestly, Derby style is half the reason we’re all here,” Madison says. And the prize? A beautiful Derby 152 bottle of Woodford Reserve. With everyone already in their finest, this is the tradition that gets the most laughs — and the most competitive.
The Derby Day Party Moment That Ties It All Together
But Madison’s favorite tradition is the simplest one: “Everyone gathers around right before the race starts, drinks in hand,” she says, raising her cocktail to the camera, “and we toast to the most exciting two minutes in sports.”
It’s the kind of moment that makes a Derby Day party feel like an event — and proof that you don’t need much more than great company, a few friendly wagers and the right bottle on hand.
Whether you’re hosting a full house or keeping things low-key, Madison’s approach is proof that a great Derby Day celebration doesn’t have to be complicated — it just has to be intentional. Start with a strong bar, lean into the fashion, and build in moments that bring everyone together.
Because at the end of the day, the best parties aren’t about where you are — they’re about how you show up, who you’re with and the traditions you create along the way.
“And remember,” Madison says with a wink, “every great Derby party starts with a bottle of Woodford Reserve.”
In addition to Madison’s tips, see here for more expert party planning tips from legendary Charleston event duo Tara Guérard and Erica Cain Missel of Soirée, and Woodford Reserve Master Distiller, Elizabeth McCall.
