Day 998 Derby Day 2025

Derby Day 2025 didn’t disappoint—with fabulous fashion, eye-catching hats, great friends, and lively horse racing, it was a day to remember. I had prepped my chocolate charcuterie board before getting myself ready and was thrilled with how it turned out… not that there’s a bad way to serve several pounds of chocolate!

My Derby dress had been hanging on my closet door for months, patiently waiting for its moment—and wow, was it worth the wait! The bright yellow radiated sunshine vibes, and when paired with a bold black feather fascinator, the whole outfit came together effortlessly. I added a little black flower clip to the waistline and wore sky-high black platform heels to keep the dress from dragging. Surprisingly, they ended up being more comfortable than I imagined (bonus: I stood tall all day)!

Our party of eight turned into six, as Carol and Gerard couldn’t join us—having already missed my birthday celebration, they unfortunately missed the Derby party too. Still, Carole and Ray brought friends, keeping our table lively, though we definitely missed the usual suspects.

One of my favorite parts of the day was seeing everyone in their best party hats—it reminded me of my son's favorite childhood book, Go, Dog. Go! “Now that’s a hat! That’s a party hat!” I used to read that book 50 times a day and could recite it from memory, most likely still can.  At the end, when the dogs had their big party, we always had to start the book all over again. If my son lived nearby, I bet he would’ve worn a party hat and joined me!

Tim, on the other hand, refused to wear a hat… but he did humor me by wearing the spectacular shirt I had picked out for him. He wasn’t thrilled about it at first, but I’ve never steered him wrong—and sure enough, he was showered with compliments all day long. Imagine if he’d worn a cool hat too!

We were all thrilled to spend a sunny afternoon with the beach club doors open, letting the ocean breeze drift in as we ate, drank, and laughed together. Huge props to Tammy, who planned the entire event perfectly, down to every tiny detail—she’s amazing!

I ended up winning Best Dressed, and to my surprise, I even placed third in the horse race!

All in all, it was a perfect day filled with sunshine, laughter, style, and sweet surprises—Derby Day 2025 in the books and one to remember.