Derby Weekend in Kentucky… The Good, The Rainy, and The Outfit Change
- Angela

- Jun 11, 2025
- 2 min read
Updated: Apr 12
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.
And somehow… every year has its own personality.
Oaks Day
Sunshine.Pink everything.
Perfect weather.
I wore pink for the survivors (that parade gets me every time), had my Oaks Lily, took about 700 pictures… and just lived my best life.
This is the Oaks we all hope for.

Winstar Farm Dinner
A whole moment.
Twinkle lights.
Dancing music.
Food that looked like it belonged in a magazine.
The salad… beautiful.
The filet… I would fight someone for it.
Add wine and good people… done.
Post-Oaks party at Winstar
Derby Day
A mess.
Cold. Rainy. Windy.Absolutely no one asked for that.
My cute outfit? Denied.
I ended up in layers, a raincoat, a random fascinator, and black rain boots.
Real classy.
But… we were with the same group of friends we go with every year, and that’s what actually mattered. Even if we were freezing.
From rain boots to rose garlands ...Derby Day delivered!
The Weekend in a Nutshell
Even with the outfit change, the rain, and the full weather meltdown… I still loved it.
Derby weekend just hits different.
The energy.
The tradition.
The outfits… even the backup ones.
The horses.
It’s my favorite.
If You’re Thinking About Going
Do it.
Go to Churchill Downs.Dress up.
Order the drink.
Stay for the race.
And if the weather turns… just roll with it.
That’s part of the story too.
P.S.
If you’ve never been and want tips… I’ve got you.
And yes… I already have outfits picked out for next year.






















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