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The Ladies Guide on How to Dress for the Kentucky Derby

Posted by Jaclyn Harris on Thu, Apr 3, 2014 @ 09:04 AM

It’s that time of year again! April is here meaning the 2014 Kentucky Derby is just a few short weeks away! Now, I know what you’re thinking. What do I pack? What do I wear? To wear a hat or to not wear a hat? Don’t worry! We’ve got you covered, ladies.

We’re going to help you plan the perfect Kentucky Derby outfit so when the first Saturday in May rolls around you’re ready! Read on to get an idea of how you should dress for the Derby this year, and don’t forget to bookmark the page so you can come back to it when you’re packing your bags in a few weeks!

The Gentleman's Guide on How to Dress at the Kentucky Derby>>>

It All Starts with the Hat!

First up on your Kentucky Derby fashion must have list is an epic hat! Horse racing draws in a unique and high fashion crowd, and since American horse racing draws from its British ties, there is a large amount of pageantry aligned with the sport. There is just as much interest regarding who attending the race and what they wore as there is about the actual race!

So what does this mean? It’s time to bring out your most elegant attire and polish it off with a hat!

Wearing a hat to the Kentucky Derby will not only add a certain class to your outfit that will help you fit in around Churchill Downs, but it’s also a great way to show your creativity! All kinds of hats are seen at the Derby! Hats donned with ribbons, bows, flowers, tulle, frills and flowers alike can all be seen inside Churchill on Derby day. And remember, the bigger the better!

Not to mention, your hat will work dual purposes to protect you from the Kentucky sun while you’re outside at the track on race day.

Plan the Attire!


Women’s Kentucky Derby fashion continues to change with the ages and becomes more modern year after year. But with that said, there’s always a sense of class and elegance to the attire to keep with the tradition of the Kentucky Derby.

Whether you’re in the mood to wear a maxi dress, short dress, flowy skirt, pencil skirt, pants or a romper, they will all be seen at the Derby. However, there are two things to remember when picking your outfit:

  1. Pick something cool and comfortable – the Kentucky Derby is held in May so the weather is likely to be warm, and once you get to the track, changing isn’t an option. You’ll want to make sure you select an outfit that you’ll be comfortable wearing all day.
  2. Plan around your Kentucky Derby hat – don’t forget that your hat is your biggest feature at the Derby! Spring patterns are fun, but you’ll want to select an outfit that doesn’t contrast with your hat. When in doubt on whether or not your outfit goes with your hat, it’s safer to go with solid colors.
And don't forget if you're also attending the Kentucky Oaks, include the color pink in your outfit choices!

Don’t Forget to Accessorize!


Accessories are a big part of dressing for the Kentucky Derby; after all, they complete your outfit! When choosing your accessories, it’s important to remember to compliment your outfit and don’t select anything to loud that it draws attention away from your main accessory, your hat.

A few necessities you’ll want to remember? A small purse to hold your personal items (you can go for a bigger purse, but remember you’ll have to hold it all day), sunglasses and jewelry! When selecting your jewelry, remember, it should make a statement, but not pull focus.

And last, but not least, footwear. When you’re seeking an outfit that screams class, it’s natural to want to pair it with your best pair of heels. But unless you’re used to walking in heels all day, we wouldn’t suggest this.

Churchill Downs is a large track and you’re guaranteed to be on your feet all day long, so search for shoes that go great with your outfit, but also offer comfort. Opt for a pair of flats or wedges that will be kinder to your feet than those stilettos. And if you are determined to wear those pumps, purchase some gel insoles to add cushion throughout the day. Trust me, your feet with thank you!

… And You’re Kentucky Derby Ready!

The important thing to remember when selecting your 2014 Kentucky Derby outfit is that you want to match comfort and fun with your own sense of style! If you have any questions about planning your perfect Kentucky Derby outfit or if you’re looking for more style tips, let us know in the comments below.

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About the Bloggers

Kristen Doolan

Kristen Doolan was born and raised a Florida State Seminole. Making her way from Florida to North Carolina, Kristen achieved her B.S. in Business Adminstration, Marketing at The University of North Carolina Wilmington. She is an avid traveler, college football addict, beach bum and loves spending time with her family and friends. 

Jazzy Morgan

Jazzy Morgan is originally from London, England and a die-hard Manchester United Fan. She grew up in Connecticut and made the move down south in 2011 where she attended Winthrop University and received her B.S. in Family & Consumer Sciences and a minor in Marketing. Jazzy enjoys traveling, working out, reading her monthly Vogue & Cosmo and keeping up with fashion trends.

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