Do’s and don’ts for dressing for the Kentucky Derby

August 31st, 2020

Choosing a Kentucky Derby outfit is just as important as picking the winning horse in the first leg of the Triple Crown.

Whether you hope to visit Churchill Downs’ historic racetrack in the future or plan to attend a low-key party at home, you’ll want to look your best for the "Run for the Roses."

This year’s Kentucky Derby is unlike any other, as the 146th running takes place Sept. 5, as opposed to the first Saturday in May.

That doesn’t mean you have to toss out the idea of pretty pastels and spring fashion, but if you want to attempt a fall Derby ensemble, go for it!

Either way, there are a few do’s and don’ts to dressing for Derby. Read below for our tips on how to steal the show with your Derby attire.

DO bring an extra pair of shoes

An eye-popping outfit isn't complete without the right pair of shoes. While it’s tempting to bust out your fancy six-inch stilettos, comfort is key during the Derby.

Many women at the track bring fold-able flats in their purse so they can alternate between formal footwear and a more casual option throughout the day.  

Take it from someone who tried walking Churchill Downs from sun up to sundown in high heels. It is not worth the painful aftermath.

DON’T go barefoot

You see it happen at the track, during a typical Derby — especially after the Mint Juleps begin to kick in. As exciting as Derby Day is, it’s also a full-day festivity that can leave you feeling tired and ready to kick off your shoes.

Resist the temptation! Even if you forget that extra pair of comfortable soles, walking barefoot will not help your feet — and surrounding spectators won't look kindly on it. No matter if you’re in the infield, paddock, or Millionaire's Row, there is no appropriate place or time to go barefoot at the track.

DO wear a hat

A tradition dating back to the late 1800s, men and women have donned spectacular head wear on Derby Day as a nod to both Southern and British culture.

Some people search for their hat first, then style the rest of their wardrobe around it. If your headgear is bold, it's usually best to go simple everywhere else. If your hat is more understated, take a bigger risk with your suit or dress.

It can be a wide-brimmed hat, fedora, beret, beanie, bowler, or fascinator. Just put something on your head.

This is the one staple of Derby. The only true fashion faux pas you can commit on this day is to go hat-less.

DON'T break the bank on it

These unique accessories can range anywhere from $15 to $800, and higher, but don’t feel pressure to go beyond your budget.

Unless you penciled in another high-fashion event on your schedule, chances are you won’t be wearing your Derby hat again for a long time.

If you do feel like purchasing a pricey statement piece, it might be wise to stop by a consignment shop to re-sell that item after the Derby. Otherwise your hat box might collect a lot of dust in your closet while creating quite the hole in your bank account.

DO dress distinctly 

Just about anything goes with Kentucky Derby fashion. Men can be seen wearing everything from baby blue, pink, or mint seersucker suits to designer duds plastered with their favorite football team's logo. (This was actually a huge trend in 2019).

Women can go for cute spring dresses, sharp pant suits, or full-length maxis. No length is too long, no pattern is too wild, and no color is off limits on Derby Day.

The more you stand out, the more you'll fit in. This is an occasion to look and feel your best as you immerse yourself in the merriment surrounding horse racing, high fashion, and Southern cuisine.

DON'T take yourself too seriously

It's easy to get wrapped up in picking the perfect Derby clothing and accessories, but don't let it overwhelm you.

While it's fun to scour the stores for showstopping apparel, it's easy to lose sight of the real meaning of Derby, if you put too much demand on yourself to outdo everyone else at the track.

You don't have to overspend, and you don't have to wear something brand new. Borrowing a hat, suit, or tie from a friend is an excellent fashion hack to keep in mind, if you can't spot that ideal outfit at the shop!

More than anything, you want to wear something that will allow you to feel confident and be fully present in the moment on Derby. Yes, the fashion is important. But above all, enjoying time with your friends, family, and the electric crowd at the track — or party — is what the Kentucky Derby is all about.

Find all your Kentucky Derby odds at BetAmerica!