My Kentucky Derby Trip!

I am SOOOO excited to share a recap of my Kentucky Derby trip with Vineyard Vines! It was seriously the experience of a lifetime.

I’ve wanted to go to the Kentucky Derby ever since I was a little girl. As some of you might know, I grew up riding horses until I was 18–my trainers lived in Kentucky (outside of Lexington, to be specific) so I would fly back there every chance I got to practice and show–horses were always a huge part of my life. My horse trainers, Bill and Nancy, were like my second parents, I spent my summers living at their house and fully embraced the Kentucky lifestyle–saying “y’all” and ordering sweet tea, and always getting “my Old Kentucky Home” stuck in my head (Bill’s favorite song of all time). Also being my parents best friends, the four of them went to quite a few Derby’s together but I was never able to go!

So basically, you could say, I’ve been waiting for my “first Derby” my whole life–and it finally came true!

When I got the invitation from Vineyard Vines, to say I was thrilled would be an understatement. I always love working with Vineyard Vines because everyone who works there is so passionate about the brand. They’ve only been in business for 20 years and have made HUGE strides in such a short amount of time. Did you catch this recent article about them in Forbes!? They have been doing some really amazing things. While they’ll always stay true to their fun, preppy staples, they’re also expanding into a lot more classic, versatile pieces as well! You’re going to love everything I wore this weekend! (Keep scrolling below to see!)

Alright, want to re-live the weekend with me?! Let’s go! (My awesome new friend Demi was our photographer all weekend–her photos are so stunning, wait until you see her photos of the race at the end!)

Friday morning yoga:

The morning kicked off with yoga on the porch of the beautiful Kentucky mansion we all stayed in–it was a really nice way to start the weekend. Can you imagine living here and having access to this amazing porch?! These yoga leggings and white tank are from Old Navy–can you believe it!? Don’t the pants look just like Outdoor Voices?

Brunch at Porch

On me: Vineyard Vines Eyelet top (TTS) white denim skirt (a little big, order a size down if you’re in between), Splendid sandals and straw pom pom bag. On Grace: Banana leaf high-low dress On Anna: white linen swing dress and raffia slides 

After yoga, we had some more coffee, showered, and changed to go to brunch and obviously took some obligatory cute photos in front of the massive columns of our Old Kentucky Home

How cute is this pom pom tote!? It’s the best because it doesn’t crush and it’s really flat and easy for packing!

Brunch at Porch! It’s a brand new restaurant in Lousville and it is as delicious as it is beautiful! I ordered the enchiladas (which they serve with an egg on top for brunch. TO DIE FOR. Also, make sure you get the donut balls!

Woodford Reserve Tour and Whiskey Tasting:

Then we hopped in the car and drove to Versailles (pronounced Ver-Sails. Not like Versailles in France, haha!) and headed to Woodford Reserve for a whiskey tour and tasting. It was really cool and I loved getting to hear all the history about the brand, property and Kentucky Bourbon in general!

Their beautiful Bourbon display in the main area! 

Woodford Bourbon Barrels 

The entire property is beautiful, and the buildings are so old–built in 1812! 

Where all of the Woodford Barrels are stored

At the end of our tour was a Bourbon tasting–I will admit, I’m not a big whiskey fan in general, but I was pleasantly surprised by how much I liked the different Bourbons and how I could really taste the difference between them all! Most shocking was that I typically hate Rye whiskey, but really loved Woodford’s! I think we should do a “Cocktails with Neal” featuring some Woodford cocktails, don’t you think!? (If you don’t follow me on Instagram, we have a little Insta Story series called “Cocktails with Neal” that is pretty hilarious–so you should definitely follow along so you don’t miss the next one (they’re usually impromptu 😂 😜)

Dinner at the Speed Art Museum

On Grace: Off the shoulder high-low maxi, Loeffler Randall shoes, On Anna: Embroidered Shift Dress, Similar black sandals, On me: Blue lace dress, Cork sandals.

After Woodford, we did another change and then headed to a special event pre-Derby dinner at the Speed Art Museum, which is absolutely stunning! The exhibit going on right now is “Women in Impressionism” and was truly amazing and so well curated.

I mean, how gorgeous and modern is the Speed Art museum? It’s newly renovated and every detail is pristine! Definitely worth a visit. (Kentucky girls…you should get married here 😜) I also was so excited to run into one of my readers, here! Hi Marissa!!

They also handed out programs and gave out a bunch of tips for picking winners! My bet was Audible, who ended up coming in third! Not too shabby I must say 😜

Derby Day with Vineyard Vines!

The big day! This is a shot of the whole crew. We seriously had such a great group. Everyone was so much fun, laid back, and truly just nice, genuine people. I might be biased but I think we also clean up pretty well decked out in our Vineyard Vines 😉

The rosé was flowing at the house all weekend 😉 Have you tried Kendall Jackson rosé? It’s one of my faves! 

On Grace: White Bow Neck Dress and Loeffler Randall Sandals On me: Ric Rac Midi Dress and cork sandals (I also want these in nude!) and pom pom straw bag On Anna: Blue lace dress (I’m styling this in a blog post soon, too!) and Sam Edelman Sandals, basket bag. We all wore this white fascinator, from Vineyard Vines designed by local Louisville designer, Jenny Pfanenstiel. Isn’t that cool?! We actually met one of her friends at the Derby. She said, “you’re wearing my friend’s fascinator!!” Haha isn’t it a small world?!

We were SO thankful to be in the Vineyard Vines area (that was tented) so we were out of the pouring rain–it didn’t let up ALL day, but that didn’t ruin our good time 😉I love all the hats in this shot! 

On Annie and I: Ric Rac Dress, On Noelle: Seersucker Shift Dress

Love my Cercone Brown girls, Annie and Noelle! They’re the PR team that planned the whole weekend, and they did such an incredible job. Annie and I were twinning! 

How AMAZING is it that the tractors were Vineyard Vines tractors?! 😂 

Love this dramatic shot that Demi took of the rain coming down. 

The Mint Juleps were flowing all day. (Okay I had one sip and couldn’t do it, but they sure made for cute photos 😂)

I love this shot–all the hats! 

The crew on the rail! (breaking with tradition, I opted for bloody marys instead of mint juleps 😂)

It got a little chilly so we all pulled on some cozy Vineyard Vines Kentucky Derby Shep Shirts! 

Every year right before the race begins, they play “My Old Kentucky Home” – which is always my favorite part. You could say I’ve been looking forward to this moment for my whole life. The song was always my horse trainer, Bill’s favorite. He was basically my second dad, who passed away last year. When I was little and imagined my first Derby experience, I always imagined being able to sing this song standing next to him, but I still felt like he was there smiling and singing with me. It was bittersweet, fun, exciting, and emotional all at the same time.  Demi was giggling at how excited I was when I heard it come on, and snapped this photo. I actually squeezed my way through the crowd by myself and stood in the aisle right next to the rail so I could get as close as possible, haha!

They’re off! Demi braved the rain and went down to the rail to get this shot. Watching the race in person was SO cool. It was so exciting watching them fly around the bend. The below is my favorite photo–I think I have to frame this so I never forget this moment!

I think I’m going to have to make attending the Derby an annual tradition! Thank you so much to the Vineyard Vines and Cercone Brown team for making my first Derby an unforgettable one! 

SaveSave