Kentucky Derby Weekend Recap

Happy Monday, friends! I just returned from a fun, fast-paced, full weekend in Louisville, Kentucky, for the Kentucky Derby. I’ve gone five times now, and every time is uniquely memorable. This time, we took some friends along with us who had never been. And experiencing the weekend through first-timers’ eyes only adds to the experience!

Plus, I’ve been experiencing so much pregnancy sickness and exhaustion (particularly bad last week) that I wasn’t sure I was even going to be able to attend. So, I was super grateful just to be there this time! Although, navigating this action-filled weekend, which happened to be extremely cold, rainy, and windy, at eight months pregnant, was somewhat comical. Ha.

Weekend Highlights

In any event, in addition to the two days of horse racing at Churchill Downs, our weekend included several other highlights:

  1. Attending the Barnstable Brown party: This black tie gala has become an annual tradition for us. And it is a truly unique experience. The party, hosted in the backyard of elderly Mrs. Barnstable, features more celebrities (actors, athletes, musicians, etc) than you can imagine. But the real fun is on the dance floor! All of these well known singers cycle through the stage, performing a “sing along”, if you will, for the crowd. This year featured names such as Boyz II Men, Travis Tritt, Kid Rock, Sammy Hagar, Bon Jovi’s Richie Sambora, and many many more. As you can imagine, singing ‘Living on a Prayer’ and ‘Dead or Alive’ along with Richie Sambora himself is pretty dang fun.
  2. Being in the winners circle at Churchill Downs: That’s right… Arklow, one of the horses in our Donegal Racing partnership, won the American Turf race on Derby Day! Indeed, that took the Derby experience from good to great. Plus, it might have helped erase a lot of betting losses from earlier in the day.

Now, given how jam-packed the weekend is, I tried something different this year… As you can imagine, a ton of thought goes into planning Kentucky Derby outfits. But sometimes the days are so hectic that getting high quality outfit photos to share here can be a bit of a hassle.

So, before I left town on Thursday, Maritere and I photographed these two looks in Houston… At least this gives you an idea of the outfits I wore. And I’ll try to share some iPhone snaps from the weekend later this week.

Kentucky Oaks Day Outfit

Now, you might have noticed I said “two days of horse racing” and I referenced outfits (plural)… One thing that many people don’t realize about the Derby is that it’s actually a two day affair. Yep, that means that one needs two great outfits — two hats, two dresses, etc.

In fact, Friday is Kentucky Oaks day. The day is headlined by the Kentucky Oaks race, which is the most lucrative race for three year old fillies (female horses). So, Friday is affectionately known as “ladies day”. In honor of “ladies day”, everyone dons pink for the day. In fact, Churchill Downs itself is transformed with all sorts of pink decorations. It’s a really lovely site to see!

With that in mind, I opted for this beautiful blush Sachin & Babi dress. Actually, as you’ll see when I share details of my baby shower, I also wore this dress for my recent baby shower. A dress so nice I wore it twice in a week to two special occasions! So, in this case, I started with the dress, then accented the look with this Karen Morris hat from the Fashion at the Races shop plus other neutral accessories.

In Closing

Did you watch the Derby this weekend? Any questions about the event? I’ve definitely learned a lot about the event and the sport in general over the last five or so years. So, I’m happy to answer any questions.

Finally, stop back by frequently this week for a big variety of content… We have lots planned, including a recap and photos from my baby shower later this afternoon, my other Kentucky Derby look tomorrow, a DIY Mother’s Day gift, a delicious recipe, and lots more.

Until next time, we wish you a great day!

Photos by Maritere Rice

Details of My Look

Sachin & Babi ‘Natalie’ dress (c/o) (similar styles here, here, and here) | Sam Edelman ‘Yaro’ sandals (also available here and here) | Karen Morris hat from Fashion at the Races (similar styles here and here) | Chanel bag (similar styles here and here) | J.Crew beaded flutter earrings | Hermes bracelet (similar styles here and here) | Jennifer Fisher bracelet (similar styles here and here) | Stella McCartney sunglasses (similar styles here, here, and here) | NARS ‘heat wave’ lipstick | OPI ‘gelato on my mind’ nail polish


  1. Jenn Lake says:

    Sounds like it was an amazing weekend! You look radiant, lady!

    1. Carrie says:

      Thanks a bunch, friend! That’s so sweet of you to say. Xo

  2. Isabella says:

    Stunning! I adore this look! I love this!

    1. Carrie says:

      Thanks a bunch, Isabella! That’s so nice of you to say.

  3. Sheri says:

    Hi Carrie,
    What a beautiful dress. I can see why you wanted to wear if multiple times.

    Next year you’ll have a little person to bring to the Derby. Can’t wait to see her outfit 🙂


    1. Carrie says:

      Ah, what a sweet sentiment! Thanks a million, Sheri. 🙂

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