An Expert Guide: How to Dress for the Kentucky Derby & Horse Race Season

An Expert Guide: How to Dress for the Kentucky Derby & Horse Race Season
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Jack Rogers Sandals

CCP's Co-Founders, Matt & Steve, Casually Watching Horses.

As it turns out, you don't have to own thoroughbreds or even know how to ride one in order to enjoy the Kentucky Derby. The pageantry, pomp, and circumstance transcend the sport, and the event's popularity stems as much from the spectacle as it does from the two minute race. And just as the jockeys must battle in their best silks when they tread upon Churchill Downs, so must the patrons don their very best ensembles as they mingle in the grandstand or the infield. That goes for Kentucky Derby parties, as well! Don't show up to the neighborhood soiree in jeans and expect to have your pick of the mint juleps. If you're going to partake of Derby hospitality, you'd best dress for the occasion.

So welcome to your fashion guide to the Kentucky Derby and Kentucky Derby parties. We'll tell you the dos and don'ts, and we'll generally put you through your paces (horse metaphor intended!), but first, as tradition dictates, it's time to get in the mood with a little "My Old Kentucky Home." Hit it! (or click here to skip ahead to the Kentucky Derby clothing collection).

Wow. That was quite moving, actually. Not a dry eye in the house (nor any empty cup, for that matter!). You might have noticed more fascinators than you even knew existed, and we were happy to catch more than a few bow ties on some of the dapper gents in the audience. But no cargo shorts in evidence. INTERESTING.

Speaking of fascinators, you might as well brush up on your vocab while you're here.

  1. a woman's light, decorative headpiece consisting of feathers, flowers, beads, etc. attached to a comb or hair clip.
  2. a fascinating person.
Basically, any piece of headwear you see at the derby is likely some species of fascinator. While we don't sell them, we do HIGHLY encourage you to wear one if you intend to attend the actual race. For Derby parties, we go with a fascinator-optional policy. If you have one, great - just don't drop it in the refreshments.
Now that everyone's in the mood for bourbon drinks and finger sandwiches, let's see some highlights from the 2018 Kentucky Derby. If you look closely, you might even see a horse or two.

Still with us? Excellent! Let's talk about CLOTHES.

Over the years, we've seen winners at the Kentucky Derby, and we've seen more than our share of losers (and we're not just talking about Barbaro...yeesh). We've broken it down (poor word choice?) to a few key takeaways. We'll start with the ladies.


  • Wear a dress. If possible, make it a seersucker dress. If not, make it a dress that you'd be excited to wear to Easter brunch or a Spring/Summer wedding. Ruffles can be your friend, but DON'T GO OVERBOARD. You can even get away with a bow if you absolutely must, but just make sure it's the kind of dress that stays modest after a few cocktails.
  • Wear a hat! When do you really get a chance to wear a hat these days? And we're not talking about your boyfriend's ball cap. Go crazy! Add some feathers. Add some color. Just acknowledge that you'll wear it approximately as often as your wedding dress.
  • Wear flat shoes. This doesn't mean boring shoes, but you're likely going to be on your feet and/or a muddy infield for a significant portion of the festivities. Even if you're in a luxury suite, though, you'll have to hoof it (get it?) from the parking lot or uber drop-off before finding any respite. On that note, you might as well invest in some Jack Rogers Navajo Sandals. There's a reason they're ubiquitous at horse races (and you can shop them via the link at the end of the article).


  • Wear a romper. We know, we know - they can be really cute, and maybe wearing shorts at an outdoor drinking event isn't such a bad idea! Just know that other people are scoffing at your foresight, and it's best not to draw the attention or derision of 1000 ladies in pearls. You've been warned.
  • Wear a hat that's wider than your shoulders. Fascinators should be fascinating, but you'd be shocked at the amount of havoc you might wreak upon bystanders while cheering for your third place horse (also known as the "show" horse).
  • Forget to wear sunscreen. Seriously. That gorgeous new dress you bought with the strappy back? It's going to leave a wicket labyrinth of sunburn lines after 6 hours of day-drinking, and we're not that far from swimsuit season.

On the ladies' side, we even have another helpful video for you. We didn't make this particular video, but we think she knows what she's talking about.

On to the gents! You might think there'd be fewer rules when it comes to men's Derby fashion, but wouldn't you know it - there are the exact same number!


  • Wear some version of a tie. A neck tie is fine. A bow tie is better. This is your chance to go a bit nuts with some embroidered silk jockeys or a four-way seersucker gingham monstrosity that is wrong in all the right ways. Remember, gents - peacocking is a good thing at the Derby!
  • Wear your most over-the-top pants or even a novelty blazer. We're talking multi-panel patch madras. We're talking embroidered thoroughbreds on Nantucket Reds. This is the time! There's no better location, and it's the ONE occasion where your wife or girlfriend has to let it slide. Carpe diem (that's YOLO for the millennials)!
  • Wear a closed-toe shoe. Yes, it may be warm, and yes, we've all seen the cool college kid in his Rainbows and seersucker pants, but if you want to be admitted to the swanky after-parties once the race is won (and trust us - you do), then you need to be prepared. Derby preparation begins with footwear. Throw on some driving loafers (extra points for horse bits), or spice things up with a white buc. Just keep in mind that your shoes will fare better in the grandstand than in the infield (as will your dignity).


  • Wear an ascot or, God forbid, a bolo. You aren't Tom Brady, and even if you were, it would still be an awful idea. See below. Now Gronk on the other hand...

Tom Brady Gronkowski Kentucky Derby

  • Wear your lady friend's fascinator. It's funny for a minute, but in a sea of dudes trying to be "the man," you'll just end up looking like "that guy." Best to avoid it.
  • Wear khakis, a white shirt, and a blue blazer. This is not a prep school social, and it's not a church. This is the Derby. The time to be conservative has passed. Dress like a champion!

Celebrities at the Kentucky Derby

Now that you know the general rules, let's see how some of our favorite and not-so-favorite celebs handled their own day in the limelight. We'll leave you to make your own judgments, but you can probably guess our inclinations. Spoiler alert: Jamie Foxx wins.

Celebrities at the Kentucky Derby

So now you have our expert tips, straight from the horse's mouth (ahem).  Remember, if you have any outfit anxiety, mint juleps are your friend, and if you're in the market for the perfect ensemble, we've got you covered. Check out our Kentucky Derby Collection below, and thanks for reading.

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The Kentucky Derby Collection


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