Your Guide on What to Wear to the Kentucky Derby®

Posted by on January 25, 2017

The months are flying by! It seems like just yesterday I was prepping you all for the 143rd Kentucky Derby® and here we stand together, moving into 2018 Kentucky Derby® talk rapidly. There are a lot of different moving parts when it comes to planning to attend the Derby. 

Where do I get my tickets? Where do I stay in Louisville? What events can I attend while I'm there? While these are questions that will incessantly be floating through your head now as we are several months out from the Derby still, there are other questions that will sneak up on you closer to the event.

Those are the questions which make us feel unprepared. The questions we don't think of until it's time to travel to Louisville. Well, this year, I'm biting the bullet to ensure you're more than prepared for when the 145th Kentucky Derby® is knocking on your doorstep in May.

I'm going to help you plan, right here, right now, what you're going to wear to the 2019 Kentucky Derby®! 

It might seem a minuscule detail now, but come April, it's all anyone will be talking about. So take notes now so when it comes time to plan your outfits and pack your suitcase, you'll be ready... ready to Derby, that is!

So without further ado, take a look at your Guide on What to Wear to the 145th Kentucky Derby®!

For the Ladies...

Now ladies, if you've spotted pictures of Kentucky Derby® pasts and celebrities in attendance, I'm sure you have a slight idea of the type of outfit you should be targeting. Regardless, I'm about to share some Derby fashion trends, as well as offer tips for comfort, so you're prepared for the long days at Churchill Downs®.

Kentucky Derby Hat

The Bigger the Better!

I'm talking about your hat, of course! Saying you will see some of the biggest, most outrageous hats you've ever seen in your life at Churchill Downs® on Derby day is an understatement. Ruffles, flowers, tulle, ribbons, bows, bright colors, wide rims, high feathers, you name it!

Pageantry is huge at the Kentucky Derby® and drawing from horse racing's British roots, it all starts with the hat for the ladies. It gives you a chance to add some creativity to your outfit and show off your personal flair. 

And do keep in mind, your hat is doing much more than adding elegance to your outfit. It's also shading your face from the Kentucky sun; no pink, sunburned cheeks for you!

The Meat and Potatoes

So not meat and potatoes, but the "meat and potatoes" to your outfit! Fashion at the Kentucky Derby® continues to change with the eras. With that in mind, your goal is to combine southern elegance with modern class.

Knee-length dresses are most commonly seen, but flow-y dress and skirts, rompers, pants, or dresses with a tighter fit are also seen often. 

There are two key things to remember when picking out your ensemble:

Kentucky Derby Attire

  1. Dress for the Weather - Kentucky May's are warm and you will be outside at the track all day long. This means, there will be nowhere to change if you are hot or cold. Therefore, ensure your outfit is something you'll be comfortable in, no matter the weather.
  2. Make Sure You Match - This might sound silly, but the more wild your hat is, the harder it is to make sure you match. If your hat is loud with crazy patterns, opt for an outfit in a solid color which compliments the hat design, and vice versa.

Comfort is Key

The last thing to keep in mind when planning your outfit is comfort is key. If you've never attended the Kentucky Derby® before, let me let you in on a secret. You're not just going to be at Churchill Downs® for an hour or two. You will be at the track from around 9 .a.m. to 6 p.m.

Therefore, if you know your feet will be killing you after wearing those heels for three hours, opt for flats. If you know you're not going to be comfortable wearing that outfit all day long, change.

Don't sacrifice your comfort for style, regardless of what the magazines say!

For the Gents...

Guys, as a general rule of thumb, you want to dress as if sophistication is meeting southern flair. You want to be suave, yet sophisticated; classy, but out of the box! 

Most gents in attendance at the Derby will be seen wearing suits, and trust me, the sky is the limit with the character you can bring in here. I'm talking bright colors, stripes, checkers, pin points, seersucker, etc.!

Whichever suit you decide to go with, just make sure your shirt and tie (optional, but bow ties are all the rage!) compliment it. As far as shoes go, I suggest Sperry's, loafers or dress shoes.

And same goes as it does with the ladies; remember, it's going to be a long day and you want to be comfortable!

Kentucky Derby Men

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2020 Kentucky Derby Official Ticket Packages