The Gentleman’s Guide on How to Dress for the Kentucky Derby

Posted by Jaclyn Harris on Thu, Apr 10, 2014 @ 09:04 AM

With the 2019 Kentucky Derby less than a month away, it’s time to start planning what you’re going to wear. While you might think that finding the perfect Kentucky Derby outfit would be the harder for the ladies and a cake walk for the gents, in realty, just as many factors come into play for the guys!

The Ladies Guide on How to Dress for the Kentucky Derby>>>

So fellas, don’t think we’ve left you out! Keep on reading so you know exactly what to bring with you to Louisville to have a rocking Kentucky Derby outfit, and be sure to bookmark this page so you can come back to it when you’re packing!

Kentucky Derby Mens Fashion

Sophistication Meets Southern Flair

One of the great things about dressing for the Kentucky Derby is that it gives you a chance to really go out of your element! Typically, when you’re thinking of a men’s outfit that is suave and sophisticated, you think of a suit in neutral colors. Guys are never really given the chance to rock bright colors and patterns in their everyday attire without getting some strange looks.

Luckily, this kind of southern flair is welcomed with open arms at the Kentucky Derby! So, check out these five tips that are going to help you select your most dapper Kentucky Derby outfit!

1. The Suit

Whether you want to go for a traditional material or seersucker, you can’t go wrong – after all, it’s more so about the colors! Don’t be afraid to try patterns such as stripes, checkers or pin points for your pants, jacket or both.

If you elect to wear a fully patterned suit or a patterned jacket or pants, be sure to pair it with a solid, complimentary colored button up shirt so your outfit isn’t too loud.

And if you’d rather select a suit that is bright and solid colored, find a bright patterned shirt to supply some texture to your attire!

As for shoes, you’ll want to choose a pair that is comfortable since you’ll spend majority of your days at Churchill on your feet. We’ve found loafers tend to complete this look the best.

2. The Tie

Whether you prefer the necktie or the bow tie, a tie is essential to looking suave at the Kentucky Derby because it is what is going to bring your outfit full circle. If you’re selecting a patterned suit and jacket, it might be best to choose a solid color tie whose color compliments your pattern.

However, if you’ve chosen just a patterned jacket, pants or shirt, feel free to choose a brightly patterned tie!

Just remember to try and only have two different patterns in your Kentucky Derby outfit – your goal is to be bold, but you don’t want to lose the sophistication element.

3. Accessories aren’t just for the Ladies

I know, I know. You hear accessories and you think that’s for the ladies! But nope, it’s time to accessorize, gents! How can you tack on the accessories to you outfit, you might ask?

Keep it simple! It’s easy to class up any attire with a fancy watch, and it IS the Kentucky Derby, so don’t rule out the idea of a tasteful hat! Find a hat that matches your suit or compliments the colors you’re wearing and you’re golden!

Another thing you’ll want to remember? Sunglasses! Although the Louisville weather is unpredictable, we’re hoping for sunshine and lots of it, so you’ll want to ensure your eyes are protected.

Final Words of Wisdom

Finally, as you’re selecting your Kentucky Derby outfit, remember that your confidence wearing it is what truly makes the attire! Take a little advice from the Kentucky Derby, “No matter what you wear, it’s how you wear it, gentlemen.”

And you’re ready! If you have any questions about whether or not you’re dapper enough for the Derby, or if you’re looking for more fashion tips, let us know in the comments below!

2020 Kentucky Derby Official Ticket Packages

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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 Administration, 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.


Evan Chronis

Evan Chronis was born in Omaha, Nebraska but has made his home in south Charlotte for almost two decades. A Tar Heel born and bred, Evan received his B.A in Media and Journalism from UNC-Chapel Hill. He is an avid Boston sports fan thanks to his family’s New England roots, and a fanboy of Wes Anderson films.