Last year, I went on the best work trip ever. I went to the KENTUCKY DERBY. Yep, I went to the Kentucky Derby for work. Best job ever. And I had absolutely no idea what to expect. For some, the Derby is an annual event for which they are planning pros. If that is you, move along and come back tomorrow. For others (like me) it is a once in a life time bucket list trip so the experience is shaped a bit differently. This is the info you really need to know about what to pack and expect.
TIP #1 - WEAR A FASCINATOR
....because when else are you going to wear a fascinator? But really though. When else, aside from a royal wedding, are you going to have an excuse to wear a fascinator?
TIP #2 - DON'T STRESS OVER YOUR HAT
This sounds a little ridiculous, I know. The Derby is ALL about the hats, right? Yes, of course. But at some point the focus moves from the hats to the
drinking horses. You might be surprised how few of the crazy derby hats you see. Most women wear wide brimmed hats that, for the most part, you can wear again. I wore this hat last year which was far closer to the norm than this one. Sorry, Erin. If you want to rock a once in a life time hat, do you booboo. But if you want to spend less than $50 and get a hat that will double as a pool hat too, know that you won't be the only one. Keep in mind derby style hats can be expensive and are blow your mind expensive (I'm talking upwards of $300) once you get to Kentucky. Plan accordingly! My under $100 suggestions are below.
TIP # 3 GET A DRESS YOU CAN WEAR AGAIN
Part of the fun is getting dressed up but there's no need to get a new dress or a once in a lifetime dress. Derby appropriate dresses can double as a wedding guest dress or a graduation dress, too. It's a long day so make sure its something you're comfortable in all day. My personal styling tip is: play with prints because now is your chance to do it!
You can do all the research in the world but at the end of the day, it's still a gamble. Maybe you know this (I didn't before I went last year) but there are actually 13 races every half hour or so on Derby day beginning at 10:30am. Each race only lasts a few minutes and in between each race, spectators retreat back inside to grab a drink and bet on the next race. A bell chimes to alert you the next race is about to start which is when you head back to your seat to watch the race. After the race is over, you head back inside to place your bets on the next race. This cycle repeats all day. You could do tons of research but part of the fun is meeting people and talking about their bets. Everyone is full of advice! I will say this though, you don't have to do your horse research but at least know the betting lingo. Sarah explains it all here.
TIP #5 WEAR FLATS
It is a LONG day during which you spend most of the day standing. Don't bother wearing heels; you'll never last. You won't be the only one in flats either. I started off in heels last year (big mistake) and I was the odd man out. Stay comfy and you will thank me later. Not completely related but this picture (and the sunglasses) prompts me to tell you: don't drink the night before. Being hungover at the Derby is not fun. Though if you are, they start selling mint juleps at 10am. Don't worry about people judging you for drinking bourbon at 10am because everyone else is drinking too. Trust me, it will help.
#6 PACK WELL
There are really strict rules about what you can and cant bring inside Churchill Downs (you can see the list here). I packed a small crossbody to keep my hands free and it was a life saver. That's the key to double fisting y'all! If you wear heels, pack a pair of flats. I wore a jacket last year and was way too hot. Pack a shawl that you can easily throw on instead.
Have you been to the Kentucky Derby before? Share your insider tips in the comments!