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How to Dress for a Derby


How to Dress for a Derby

Most of us feel a little nervous when we’re getting ready to attend a fancy event. What if we look out-of-place, or aren’t dressed quite right? There is one social event in particular that might be very confusing in terms of clothes… no, not Burning Man… it’s a horse race!

Let’s start out by acknowledging the obvious. Some horse race tracks are seedier than others, some have an air of tradition about them, and PETA says the whole affair is cruel. But if a horse race is where you find yourself, here’s how to dress like a winner… with visual inspiration from two accomplished women, Sydney Sweeney and Barbara Corcoran.

If you physically go to an actual derby, ideally after the pandemic is over, make sure to check if the organizers have rigid rules on what to wear. The more prestigious tracks might have a strict dress code.

That’s right, even though this is a race track, not a red carpet, it’s definitely a potential occasion to dress up. And as a matter of fact, this year, the Kentucky Derby got better ratings than the Oscars!

Best Horse Rider, an online publication dedicated to this subject matter, points out that this kind of sports event can even turn out to be a “fashion-mecca” where people are expected to wear their “Sunday best!”

If you are among the chosen ones to attend the Royal Ascot that happens every June at the Ascot Racecourse in Berkshire, England, be ready to see the Queen who officially opens the event each day. Lifestyle magazine Town & Country describes the experience as a “cross between a royal wedding and the Kentucky Derby.”

As you could have guessed, the dress code there doesn’t allow any slack. Among socially acceptable pieces of attire are modest dresses (above the knee or longer) or pantsuits that are full-length to the ankle and of matching material and color. Off-the-shoulder or halter neck tops and strapless dresses are not allowed at the Royal Ascot. And the straps themselves have to be one inch or wider. Yikes!

A hat is also a must at this event. However, you can’t get too funky with it — “novelty hats” are prohibited, along with any hats that are unreasonably oversized, and anything that is endorsing or marketing any product or brand.

Coming back to the USA, derby fashion traditions and trends can still be observed but tend to be less demanding. There are “no hard and fast” fashion rules! It’s not LittlePinkTop saying that; this is actually the official guidance of the Kentucky Derby.

The famous American horse race also points out that your outfit will be influenced by where you plan to spend the day. Suppose you got reserved seating such as a grandstand, clubhouse, suites, or corporate hospitality area. You’re expected to wear pastel-colored clothes and a fancy hat is a welcome touch.

But there is a huge distinction between the grandstand and the infield. The latter has been described as muddy grounds for mayhem and general exhibitionism

If you don’t want to get dragged through the mud, literally and metaphorically, here’s what to do, and what to avoid, in order to look like a seasoned derby goer.  


  • Find a classy dress in a soothing color. A well-cut knee-length dress is a safe bet. You can always pick a slightly longer option, too. Look for a delicate color such as pink, mauve, baby blue, magic mint, peach, periwinkle, or lavender.
  • Get all fancy with an elegant hat. You may color-coordinate your hat with your dress or choose a unique piece that will make you stand out from that socialite crowd. Usually, ladies wear wide-brimmed, “Southern Belle” hats. They can be decorated with flowers, ribbons, feathers, and cute bows. Here comes your chance to express your individuality. In case you need to get an impeccable hat, check out Bijou Van Ness. They carry a variety of choices that are just pure sophistication.
  • Wear dressy but comfy shoes. Heels, platform sandals, or sophisticated flats all work. The only requirement is to be comfortable and find something that goes well with your overall outfit. Remember, the day is long! You might need to cover great distances. So, pick a pair of appropriate shoes. And if you are at the infield, maybe go for Hunter boots.  
  • Be minimalist with your jewelry. Keep it simple here, especially if you are already wearing a hat. Classy earrings, maybe a dainty necklace, a watch, or a delicate bracelet are more than enough.
  • Bring a fancy clutch in a functional bag. I know you might not want to have a large hat and a large bag, but you have to be practical here. You will spend a whole day at the race track, so you will probably need your phone, your program, a bottle of water, sunglasses, sunscreen, and maybe even spare shoes or flats in case you end up walking across different terrain. There is a limit to your bag size, though — each guest is permitted one bag no larger than 12″ x 6″ X 12″ at Churchill Downs Racetrack.


  • Don’t wear a formal gown. A horse race can sometimes be a classy event but it’s not Buckingham Palace.
  • Don’t go in sneakers, sweatshirts, or sweatpants. Does this go without saying? I hope so. Also, don’t wear anything that looks like you’ve been clubbing all night long.
  • Also, don’t go overboard with that fancy hat. Get off your high horse, girl! There’s a difference between something that’s fancy and something ridiculous. M-O-D-E-R-A-T-I-O-N is key here.  

Sydney Sweeney definitely passed this unique fashion challenge while attending a race track in the U.S. recently. She posted her look to Instagram Stories.

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Sweeney wore a strappy green dress. It looked very romantic, in the best cottagecore traditions. She chose beige platform sandals that couldn’t have been more appropriate. They looked fancy yet comfy. This is a winning look!

Do you want to channel your inner Southern Belle, too? You can do it even without going to a horse race or actually being from the South! This is what real estate magnate Barbara Corcoran did!

As viewers of “Shark Tank” know, Barbara can be very sharp, straightforward, and witty, and you can also see that in her recent post about derby fashion. Barbara posted something in the “Instagram vs. Reality” meme format.

The first image showed her at the actual Kentucky Derby in the past, wearing a fancy green hat. The “reality” photo showed her goofing around at home, wearing a simple white shirt, pink blazer, and a yellow, eye-catching cambric with feather bowler all while pretending to ride a stick pony.

Barbara even ran around a table in her home and suggested that it was part of her new workout routine. Barbara captioned the post: “Practicing for the #KentuckyDerby today! How’s my form? 🤣🐎”

Follow the example of the nation’s beloved shark, and don’t forget to dress up, even if you are staying at home. And look even better in reality than you would for a filtered Instagram post!

You know what they say: you can lead a horse to water, but you can’t make it drink. LittlePinkTop just provided you with some styling advice, and now it’s your turn to win this fashion race.

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