The Kentucky Derby was always on my bucket list! Last year I was able to fulfill that wish thanks to my sweet husband! Josh surprised me with tickets to the derby. I couldn’t believe it! I was finally going to the Kentucky Derby!
First a little backstory…Natural disasters seem to follow me when traveling. I don’t know why but it started with our honeymoon in 2005. A hurricane turned into a tropical storm and it rained the entire time we were on our honeymoon. While shopping for the derby I had no idea it was going to be the coldest and wettest derby in like 70 years. I was having a blast shopping for the derby. However I had to do some research first.
So what is the proper attire for the derby??
Dress: Any sort of spring dress. You want to go for colorful if possible. Not only do the women wear colorful clothes but the men do as well. Crazy patterns are okay too!
Shoes: A great spring heel or sandal. You will be doing a lot of walking so keep that in mind when shopping for shoes.
Jewelry: No real need for a large statement piece. I would say a great pair of earrings and minimal jewelry or small jewelry for bracelets and necklaces. The hat is the main focus so you don’t want to draw attention away from it.
The hat: Wearing a hat to the Kentucky Derby is believed to bear good luck! Like I said, this is the main focus! You must find a great hat! It doesn’t have to be huge and outrageous but it can be if that is what you are going for. You can also wear a fascinator. I will show you my favorite pics for these below. As for hats they can range from super affordable to absolutely crazy expensive. Picking a hat was the hardest part for me. We got our tickets in mid April so shipping time was also a factor. I didn’t have a bunch of time to get it shipped here. There aren’t really any derby hats around Oklahoma City that I could find at this time. I knew I wanted a hat that was comfortable, stylish, and hopefully unique and would stand out without needing to have giant decor and of course I needed something affordable.
Side note: My hat ended up being famous! Nobody had my hat. I couldn’t believe it! It was simple, beautiful, comfortable and most of all affordable. My hat had the famous derby saying “hold your horses” embroidered on it. I was walking around on derby day and my husband would say don’t move Kristi. I had news channels and photographers following me around snapping pics of the back of my hat. For a few minutes I felt like a celebrity and it was fun! I even found my hat on news station posts after the derby all over the U.S. My hat was famous! : )
The handbag: They have a size limit. On the website they say they will measure your bag at the entrance. I stressed about this because every bag I wanted to use was too big. I even called ahead just to make sure that they actually check. They told me yes they are strict. Guess what??? They didn’t even check!!! Of course being the rule follower that I am I just went for a small crossbody because I was worried they would say your bag is too large and not let me in. Maybe it was because it was pouring rain and they were rushing so they didn’t check bags…. At the end of the day I’m glad that I didn’t bring a large cute bag. My crossbody fit under my raincoat and didn’t get ruined so I was glad. Also on the subject of bags. The only thing I hated about the derby is the insane amount of people smoking cigars. It was awful! It’s a derby day tradition and they make tons selling cigars so sadly I don’t see this changing. I was so glad I didn’t have one of my designer purses with me because I’m sure between the rain & the cigar smoke they would be ruined. Prepare yourself mentally for the smoke if you are like me and not a smoker and get headaches from smoke.
What I wore: I ended up wearing a Lilly Pulitzer dress, a Draper James hat, Stella & Dot jewelry and instead of my cute sandals I wore Joules rain boots & a raincoat…. Yes I said rain boots & a raincoat. I was super bummed but it was so cold and it was pouring. I have never been so thankful to have covered seats as I was for the derby. I can’t imagine having the seats right in front of us with no cover, waiting all year for it and then it pours almost the entire time! We didn’t get to do as much walking around as we probably would have because of the rain. The first day we got to go to the Oaks races and I wore a bright pink dress that I found on a whim at Kohl’s of all places(I never shop there unless it’s for the kids), a jacket from Athleta & my Joules rain boots. On the Oaks race day I wore my hair down and straightened. Sadly nothing amazing due to rain. It was so humid from the rain that if I didn’t use a flat iron and get the heat on my hair it would be a giant frizz ball. On the derby day I curled my hair and it stayed pretty well. You are wearing a hat so your hair should be simple. A side low pony tail or a side braid would look amazing with a hat or fascinator. Keep it simple!
If you are going to the Oaks races which are the day before the derby make sure you shop in all the stores on this day. You won’t regret it. I bought all souvenirs (shirts, hats, gift for the kids) and was so glad I did. On derby day it’s so crowded that you will have to wait until enough people exit a store to even get to go in and shop and then there are still the long checkout lines. If you are only going to the actual Derby day only then get your shopping done as soon you get there. You won’t regret it!
The red carpet!!! If you are like me and love to read about celebrities and follow them on social media then you must make your way to the red carpet celebrity entrance on derby day. Make sure to have your camera with you! I think personally they should have some sort of stands set up for us regular non famous people to watch the celebs enter. Sadly it’s only an area that you stand and hopefully get a great spot hopefully on a slight hill so you can see. If you are tall then you are good to go! My husband didn’t really get why I wanted to go watch the celebs enter but he stood there with me and waited.
PLAN WAY AHEAD IF POSSIBLE! Since we got our tickets in mid April everything was already booked. Finding a hotel room available that wasn’t 4 hours away was impossible! We decided to try Airbnb since it was all we could find. First let me start by saying everything on Airbnb was also booked minus a few here and there. The prices were inflated a ton as well. We ended up booking a “studio apartment” for $250 a night. I think it usually booked for $60 a night but we had no choice. The pictures looked ok so we booked it.
Our flight was delayed so we didn’t get to the Airbnb until 10pm. It was in the middle of nowhere (was supposed to be right next to a park) and it was pouring rain. We pull in and are immediately out of our comfort zone. The look on Josh’s face was priceless. I think I even remember him saying lets go buy a tent. I looked at him like are you insane?? We were greeted by a very nice man that proceeded to show us into his home to the “studio apartment” inside his actual house!!!! We were under the impression that we had the whole place. He said we live down here and the apartment is up there. We walked up the stairs and he used the keypad to open the apartment door. We said goodnight and entered the apartment. First of all there was no way to lock the strangers living downstairs out of the apartment! Second the bathroom had no curtain in the window so anyone could look up and see you after you got out of the shower. The beds were two twin beds and horrible. In fact the headboards weren’t even attached and looked like if you bumped them they would fall over. Everything in it was ancient. From the tiny kitchen area to the toilets. I will say it was clean though. Needless to say we were so uncomfortable. We talked about leaving but we couldn’t find anywhere else to go. We were able to book the second night at a nice hotel about 1.5 hours away from the derby. I don’t think either of us really slept that night. We were worried about someone just walking in during the night. Josh being the engineer that he is created a sort of “trap” so if someone opened the door a jar of spices would fall and break to wake us up. LOL! The next morning we got ready for the Oaks and snuck out really early so we wouldn’t wake the family sleeping downstairs. This made for a very tired, cold, rainy Oaks race day. Derby day was so much better and much more fun for us since we had a good nights sleep at the “real” hotel. I have nothing against Airbnb and know many people who use it regularly and love it. This was just not a good experience.
This year outfit recommendations:
Vineyard Vines the official style of the Kentucky Derby, has created a line of dresses just for the Kentucky Derby. I called them today because I haven’t seen this years line yet and they told me it should be released in early April. You will see more of the Vineyard Vines outfits only because it’s the “official brand” for the derby. So if you want to stand out a little more then go out and pick your own outfit that isn’t this brand. I personally think Lilly Pulitzer has tons to choose from that are perfect for this day. I have created a Pinterest board for hats & dresses for derby day! You can follow me on Pinterest and shop through my board. Leave a comment with your derby day pics! I can’t wait to see what you end up wearing. Have an amazing time and I hope it doesn’t rain this year!
Here are some pictures of Josh & I from last years derby as well as some pics of the crazy hats I saw!
Picture of the dress I wore last year. I realize you can’t see the entire dress due to my jacket.