Derby & Oaks: Sunshine, Raincoats & Real Life Fun

Derby weekend in Kentucky is basically a state holiday — an excuse to dress up, drink something pretty, and cheer for horses like we own them. 😂

This year gave me two totally different vibes.

Oaks Day:

Sunshine, pink everything, perfect weather. I wore pink for the breast cancer survivors (the parade gets me every time), drank my Oaks Lily, took 700 pictures, and lived my best life. Truly the Oaks we dream about.

Oaks Day vibe ...sunshine, pink, and perfect weather.

Winstar Farm Dinner:

A whole moment. Twinkle lights, bluegrass, and food so beautiful I took photos like I was opening a cookbook. The salad? Gorgeous. The filet? I would fight someone for it. Add wine + good people and it was chef’s kiss.

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

Derby Day:

A mess.

Cold, rainy, windy… absolutely no one asked for that. My cute spaghetti-strap outfit? Denied. I ended up in layers, a raincoat, random fascinator, and black rain boots. Real classy.

BUT… we were with a great group of friends we go with every year, and honestly, that was the best part... even while we were freezing.

From rain boots to rose garlands ...Derby Day delivered!

The Weekend in a Nutshell:

Even with the outfit swap, the rain, and the full weather meltdown, I still loved every second. Derby weekend just hits differently...the energy, the tradition, the clothes (even the emergency outfits), the horses… it’s my favorite.

If you ever get the chance to come to Kentucky for Derby weekend, go. Hit Churchill Downs, dress up, drink something fun, and soak it all in.

And if you’ve never been and need pointers, message me. I’ve got plenty of tips and a couple of outfit fails ready to share.