Dubbed the “Run for the Roses,” The Kentucky Derby is the longest-running sports event in America. The event was first held at Churchill Downs racetrack in Louisville. It features three-year-old thoroughbreds racing a distance of 1.25 miles. 

The Derby unfolds every year on the first Saturday in May. About 150,000 glamourous racing fans arrive at Churchill Downs wearing their colorful (and oh-so-flamboyant) frocks. The Kentucky Derby is sometimes referred to as “the greatest two minutes in sports.”

Aside from placing bets on their favorite horses, you’ll witness Derby fans singing “Old Kentucky Home”, sipping on the famous mint juleps, and of course, showing off their over-the-top hats! 

But how can you put together a jaw-dropping outfit for the day? Dive right in to find out. 

Outfits You’ll Typically See People Wearing 

A Southern charm spreads across the scene at Churchill Downs on the Kentucky Derby weekend. The event is nothing short of a fashion spectacle. From breezy spring dresses to gorgeous, fitted suits – you’ll see the ladies putting their best style cards forward here. Remember, you don’t want to be caught “hat-less” at the Derby. When it comes to the dress, you’ll witness lots of floral or solid-colored pieces.

The boys typically go all out in their lightweight jackets and slacks, Bermuda shorts, luxurious silk traditional tie, or a southern-inspired bow tie. 

Where you’ll be sitting during the event also plays a role in the type of outfit you’re going to choose. The important thing to remember is that the derby takes place in Spring. So, consider outfits in pastel colors for those insta-worthy looks. 

Finding Your Own Show Stopping Outfit 

The importance of wearing your fanciest Kentucky-Derby-worthy hat cannot be stressed enough, but your dress commands an equal spotlight. Fortunately, there are just a few easy-to-follow choices that help narrow down the range of dresses you can choose from. 

For the dress, you have three solid choices – single-colored dresses, heavy floral pieces, and stripes or polka dot designs. If your mind oscillates towards a heavy floral pattern, make sure you team it with the right hat. Most Derby Hats feature a generous dose of florals, so pick a dress to match those. If you choose to go with a single-colored dress, make sure you choose a bright or a pastel hue.

Now, for the length of the dress, you have three choices – just above the knee, knee, or mid-calf. By far, the most popular ones feature a 50s style A-Line pinched at the waist. Why? A-Lines are made to flatter most body types.

Finally, when it comes to necklines, a Bardot neckline is another ultra-popular option. The official flower for the Kentucky Derby since 1904 is the red rose. So, naturally, dresses in red are often popular (and encouraged) but not mandatory.

What Accessories to Flaunt? 

A well-rounded Kentucky Derby ensemble would include a gorgeous dress, a flamboyant hat, a bag, shoes, and jewelry. Let’s discuss how you can put together a great outfit:

The Hat 

What truly sets the Kentucky Derby aside from a million other sports and entertainment events? Is it the best-trained thoroughbreds? The romantic Twin Spires? The Hollywood celebs? Well, maybe, but first and foremost, it is the hats! Call it part spectacle, part Southern tradition – the Kentucky Derby Hat parade is what truly makes the event “The Greatest Two Minutes in Sports.” From delicate to fantastic – there are simply no limits to the type of hat you can choose. 

This age-old fashion tradition was initially started by women and remains beautifully preserved even to this day. After all, wearing a hat is much like getting into a costume. You’ll be surprised to see the type of personality your hat lets you take on!

Those in the Churchill Downs Infield simply go all out with their hats. You’ll find hats in all shapes and sizes – some even bring humorous themes alive! On the other hand, within the sections of Churchill Downs, you’ll spot hats that speak the tales of elegance and style. The most popular hat choices include the “Southern Belle” inspired wide-brimmed Derby hats. The hat décor includes ribbons, feathers, flowers, and bows of any color. 

The Bag

Prepare for a long day when you decide to hit Churchill Downs. There will be lots of prep and packing. You might want to carry a large bag but not over the size limit. The official Kentucky Derby website makes it clear that “Each guest is permitted one bag no larger than 12" x 6" x 12."

The Shoes

Sandals or spring heels are two of the most wildly popular choices for the event. Remember, the day is long, and the historical grounds are tricky to navigate. So, be sure to carry another pair of flats (just in case)!

The Jewelry

Since your hat is undoubtedly going to steal the show at the event, it’s best to avoid any statement jewelry pieces. Keep it simple with the ornaments or go for Kentucky-Derby-themed jewelry. 

A Few Words of Wisdom 

With your dress, hat, and other accessories figured out, let’s discuss some valuable tips you might want to remember.

Leave your stilettos at home if you want to stay comfortable throughout the day. Skip your shapewear and go with a looser dress if you don’t want the sun to end up engulfing you. Athletic shoes and jeans might seem like comfy options but are simply not appropriate for this fancy event. 

Remember, you’ll be out in the sun for nearly 12 hours. So, do not forget your sunscreen. To keep your makeup well-preserved and fresh throughout the day, make sure you invest in a makeup setting spray. Finally, remember to downsize your purse if you don’t want to let a heavy, gigantic bag come in the way of enjoying the race and your mint julep!

That said, have you decided on the dress you’d be wearing for the Derby yet? If you haven’t made the decision already, we suggest you head over to NewYorkDress right now, explore an endless array of Kentucky-Derby-worthy dresses from high-end fashion houses, and make your pick!