🐎 Derby & Oaks: Sunshine, Raincoats & Real Life Fun

Every year, Derby weekend is basically a holiday in Kentucky — and let’s be honest, it’s one of the best excuses to dress up, sip something fun, and spend the day cheering on horses. This year, though? It was a weekend of two very different vibes.

🌸 Oaks Day — Pretty in Pink & Picture Perfect

Oaks was everything you dream it’ll be: sunshine, color, and fabulous fashion. Everyone wears pink (it’s tradition!), and this year, the weather actually cooperated. The sun was shining, the air was warm, and it was the kind of day where you want to take a hundred photos because everything just feels like a celebration.

I wore a pink outfit in honor of the breast cancer survivors — one of the most beautiful traditions of the day. They even hold a Survivors Parade, and it’s one of those moments that really hits your heart. Between the drinks (hello, Oaks Lily), the food, and the people-watching, it was one of those rare days that lived up to the hype.

Oaks Day vibes — sunshine, pink, and perfect weather.

🍽️ Winstar Farm Dinner — Fancy Food & Country Vibes

After the races, we headed to the Winstar Farm Derby party, which is one of my favorite things we do all weekend. It’s out at this gorgeous horse farm with twinkle lights, live music, and food that makes you want to take a photo before every bite. (Which, yes, I did.)

We started with this beautiful butter lettuce salad — radish, cucumber, tomatoes, feta, and a little crispy bacon on top. Light, fresh, and totally plate-worthy.

Insert salad photo here

Then came the star of the show: a filet mignon that was perfectly cooked and served with roasted veggies and these gorgeous sauces — red wine reduction, herby green purée, and something sweet and savory I couldn’t quite name but definitely didn’t leave behind.

Insert filet photo here

Pair that with a glass of wine, some live bluegrass under the stars, and the best people? It was the perfect end to a picture-perfect day.ay.

Post-Oaks party at Winstar — food + live music = yes, please.

🌧️ Derby Day — Cold, Wet & Still Worth It

Now Derby day... that was a different story. The weather took a hard turn — rain, cold, wind — and I knew pretty quickly that my cute outfit plans were not going to survive.I had planned to wear a spaghetti strap jumpsuit — you know, the cute kind you wait all year to wear. But between the cold and rain, there was just no way. I had to pivot fast. I swapped to pants, layers, a raincoat (yes, sleeves!), and dug out a fascinator I’d never worn. Add some trusty black rain boots, and I had my last-minute Derby look.

Bonus? We were with a group who actually had a horse running in the Derby! It didn't win-but just being that close to the action made it feel extra special.

From rain boots to rose garlands — Derby Day delivered! 🐎👒🍹 Cheers to mint juleps, last-minute outfit changes, and a winning view of the track!

🍷 Drinks, Bets & a Little Bit of Chaos

Between Oaks and Derby, we definitely had our fill of great drinks, fun moments, and a few (not-so-winning) bets. I always go in with a few favorites and a few random picks just for fun — and sometimes they surprise me! The food at the track never disappoints either, especially when you’ve been walking in rain boots for half the day.

💛 The Magic of It All

Even with the outfit swap, the cold, and the change in plans, it was still everything I love about this weekend: the energy of the crowd, the tradition, the excuse to dress up (or pivot entirely), and the chance to just soak it all in. Derby weekend has a way of reminding you that sometimes, the best memories come from the unexpected.

💬 Your Turn!

Were you at Oaks or Derby this year?What was your favorite moment… or your funniest outfit fail?Already planning next year’s look — and yes, rain boots will be included. 😉