Here are details from the rest of my trip in Louisville.
The Kentucky Oaks! As I stated before, the Oaks is a race of 3 year-old fillies held at Churchill Downs and people are asked to wear pink to bring awareness to breast and ovarian cancer. My friends and I started a tradition of wearing fascinators to the race and calling it fascinator Friday and saving the big hats for Saturday. I was SO excited about my entire outfit! Unfortunately, the weather was terrible! The locals were saying they had only seen one other time where the weather had been that bad 😩 It was really cold, windy, and rainy. My friends and I were pretty disappointed, but we sucked it up and put on our fabulous outfits. I brought a cardigan just in case it was cold and it helped a lot. The weather is known to be unpredictable that weekend so ALWAYS take something cute you can throw over your outfit.
I loved that my dress had a train, but it dragged a tiny bit and people stepped on it a few times 😢
We bought seats this year, but they weren’t covered and it was so cold that we didn’t even use them. It was much warmer to stay in the paddock area where there are crowds of people to trap in the heat. The Oaks isn’t as crowded as The Kentucky Derby, but it’s still a blast and you meet a lot of awesome people. I would definitely recommend going.
For dinner in the past we’ve gone to Jeff Ruby’s which is a staple in Louisville. It’s got a great ambience and even better food. It’s always packed with people from out of town excited about the derby the next day. It almost feels like a big party. It’s VERY hard to get a reservation here. They open up reservations for about an hour in January and get booked ridiculously fast. This year unfortunately, we must have missed the date because by the time we called they said they were booked. Honestly I was pretty bummed about it, but was also excited to try some place new. We decided on Vincenzo’s and were really pleased with it! It didn’t have the “party” atmosphere that Jeff Ruby’s has, but it was a beautiful restaurant with excellent service. The food was delicious!
This dress was my favorite night dress I wore. The white, the purple florals, the off the shoulder! I just loved everything about this dress. It’s no longer available online, but I got it at Agaci and it was around $30.
We went to two parties. The first one was the Fillies and Stallions party. The first year we went it was sponsored by Maxim so it was full of tons of celebrities (mainly NFL players) and is a really popular party. It’s no longer sponsored by Maxim, but still has the same amount of turnout. This year it was sponsored by Patron Tequila. This year I saw Aaron Rodgers and Jimmy Garoppolo and some others that were there were Julian Edelman, Danny Amendola, Chace Crawford, Josh Henderson, Tony Romo, and Tom Brady (I would have died to see him 😍). One thing I learned about going to the derby is that having hookups is essential! As soon as you decide you’re going tell anyone and everyone that you’re going and you’d be surprised by the feedback you get from people. The first year we got into this party was because one of my friends’ sister used to work with a guy who was hosting the party. We’ve been on the email list ever since. Although, each year you have to email them a picture of yourself to be considered an “ambience” model and to get in free. A cute thing about the parties is since there’s so many celebrities in town they always have a red carpet with a backdrop ready for you to take pics in front of.
A couple of things they had this year that I didn’t remember them having before was a photo booth type of area and a make-your-own-hat station!
The second party we went to was the DerbyVIP party that was sponsored by Grey Goose and held at The Gramercy. All these parties you either have to know someone to get in or you have to pay quite a bit of money. One of my friends that was going happened to mention to her hair stylist (she’s from Louisville) who also happens to be her neighbor that she was going and she got us connected with a promoter who got us into all these parties for free! So like I mentioned before, get the word out that you’re going because you never know who may be able to help you out.
My one and only celebrity photo-op was at this party with Tyron Smith of the Dallas Cowboys. Honestly my friends and I usually come home with a handful, but sadly this year there just wasn’t many opportunities to take any photos.
Happy Derby Day (that’s everyone’s greeting for the day 😊)! The day was finally here! The Kentucky Derby! The weather at The Oaks was so terrible that as a group my friends and I decided that if the weather was the same that we would just show up at the derby with jeans and sweaters on! THAT is how miserable we were on Friday. We were all so sad about possibly not wearing our adorable dresses. Luckily the derby Gods were looking over us and the clouds cleared and the sun came out on Saturday! 🙌🏼 The temperature rose and there was no rain OR wind so we got to wear our outfits! On a side note, I told you guys about those green heels I ordered and was waiting to see if they matched my hat to decide if I’d wear them. Well they matched perfectly and I was so pumped about them, but I put them in a pocket in my suitcase that I don’t usually put shoes in and I totally forgot to wear them! 🤦🏻♀️ Anyways, so picture my outfit with the cutest matching green heels 😉
I forgot to mention that with any big event you can only get dropped off so close to Churchhill Downs and then you have to walk. We actually got dropped off at a gas station and had to walk several blocks. Another reason why you should take my advice and wear low heels!
They have bag restrictions that only allow a bag to be 12 inches in each direction. I was able to bring my backpack which was great because not only was I able to carry my rolled up flats in there , but I was able to carry a couple of the other girls’ flats too. I also didn’t think it took away too much from my outfit and easily took it off for most photos. I’d definitely take a backpack again.
The Kentucky Derby is like The Oaks…times 10. There’s a lot more people, the hats and outfits are more grand and people are having a REALLY good time i.e. lots of alcoholic beverages being consumed. Of course the famous drink of the derby is the mint julep. I personally am not a fan of the drink. A little too strong for my taste. I actually drink the The Oaks Lily, which is served at both race days. It consists of vodka, sweet and sour mix, cranberry juice, and a splash of triple sec. It may be too sweet for some, but it’s straight up my ally. You also get to keep the commemorative cup and since I brought my backpack I actually brought one home this year!
We didn’t buy seats this year because in the past we only sat in them during the race which is about 2 minutes or we’ve met people who have invited us to their seats which is what happened this year.
Time for the race! The main race ended up being around 6:45 (we got there around 1). Betting can be kind of confusing, but with a little reading and help from friends I placed several bets. I actually won one of my bets! I placed a bet on the winning horse, Always Dreaming. Unfortunately, it was a favorite so you had to bet a lot to win a lot and I lost on a few of the earlier races so in total I lost $100. Oh well. Betting makes the races more exciting so I’m glad I did.
We left dinner open for tonight and were just going to play it by ear. By the time we got back to our hotel it was kind of late and everyone was tired so we ended up just ordering pizza. We went to our last DerbyVIP party sponsored by Stella Artois and held at 8up. I honestly was pretty tired from the previous nights. Did I mention that some of the bars stayed open til 6am! Some of the girls (including myself) took advantage of that Thursday night and I was still hurting from that. I didn’t want to skip the last night though and I DID have one last cute outfit to wear. This yellow dress I thought was so bright and fun and perfect for spring. The ruffles were kind of hard to adjust. I meant to iron them down really good, but didn’t have time. Still a great dress if you want to stand out! I’m glad I went because I met Demarco Murray and Tony Romo! Chace Crawford was there too, but I didn’t get to meet him. I didn’t ask for any pics though because we were in VIP when I met them and the vibe was a little more relaxed so I didn’t want to bug them.
We always do brunch before we head to the airport. In the past we’ve gone down the street to the bigger Marriott because they have a brunch buffet. This year we decided to change it up and went to a local pub that served food. I can’t remember the name of it 🙈 We were near Main St. and there were several other cute places with patios that we passed on the way. It was the perfect food after a weekend of cocktails. Cheese fries, burgers etc. After brunch we got on the road and drove the two hours back to Louisville. This picture describes perfectly how I felt on the flight back…just absolutely tired and ready to be in my own bed. At least my dress was cute 😂
The trip was a great time and we had a lot of fun. The only thing I wish we would have done was go to 4th Street Live so the girls who hadn’t been to Louisville before could have seen it. It’s an area of bars and restaurants that are within walking distance of each other. It’s similar to 6th street in Austin except it’s a little cleaner and an older crowd (at least it is during derby weekend). We had specific plans each night and a party to go to so we skipped it, but if you find yourself with some free time you should definitely check it out. The Kentucky Derby is definitely a trip everyone should take at least once. I hope you guys enjoyed my first little travel diary!