Refined Eloquence: 15 Outfits to Wear to the Kentucky Derby

By Shelby Bonner Mar 17, 2024

The legendary Louisville-based horserace is celebrating 150 years in May 2024. The Kentucky Derby is the most famous and most-watched horse race in the United States, bringing over 150,000 guests each year.

All though the actual race only lasts a few minutes, the Kentucky Derby is a full-day event, with social events and parties. It is also a place to dress to impress and creates a stage for women and men to show off their bold looks, and fashion style.

Based in the south, many looks have a classic southern charm combined with a more urban edge. Outfits are both refined and eloquent, as well as daring and fun. It is a rare chance for many to dress up and attend an event looked forward to every spring.

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Dress Code

Depending on what part of the Derby you are at, certain dress codes are in place. Business casual dress is expected in most places, with denim, athletic shoes, shorts, t-shirts, or athletic wear not allowed. Casual wear is permitted in the Clubhouse but is not a common practice.

Find more clothes to wear at a race here.

Clothes for Sitting Outdoors

Unless you are in a private box, you are most likely going to be sitting and standing outdoors in the elements for most of the day. Consider bringing light layers to wear in case it is windy or rainy. Also, consider clothes that can be worn in the grass and dirt without easily being stained or ruined.

Try out these outdoor brands.

Muted Dress

If you want your hat to be the star of the show, many women opt for a more neutral, muted dress that won’t compete with their hat. Choose a solid color dress in a neutral or pastel color that compliments your hat. Also, consider a simpler fit such as a belted or midi dress.

Check out these affordable dresses.

Bold Dress

On the other hand, many women want their dress to take center stage, and opt for a subtle hat that compliments their dress. Go for bright colors, bold patterns, and more dramatic styles, such as flowy maxi dresses, fit and flare, and ruffled styles.

Discover these dresses.

Head-Turning Hat

In the 1800s, when the Kentucky Derby first began, hats were the standard attire for women and men. Nowadays, hats aren’t as common, but the Derby provides a rare opportunity to wear one. Hats are also thought to bring good luck to whichever horse you are cheering for.

Many women take the opportunity to choose a large, bold hat with many adorations and decorations to create a stunning, head-turning look.

Find more hats here.

Hat for Men

There are fewer hat options for men than there are for women. The majority of men at the Derby opt for a lightweight straw bowler or fedora-style cap. The straw material will not overheat you or weigh you down, while still working with whatever you choose to wear.

Discover more places to wear a hat here.

Fascinators

If a large hat is not for you, a great alternative is a fascinator. A fascinator is a smaller headpiece worn on a headband or comb. They can be just as eloquent and detailed as a traditional hat, without being as large and heavy.

Fascinators have become more popular at the Kentucky Derby with many British royal family members dawning them as they attend this legendary race.

Try out these hair accessories.

Practical Sandals or Heels

You will most likely be on your feet for most of the day, so choosing practical shoes is a must. Many women go for comfortable sandals or chunky espadrilles that complement their dresses and are perfect for spring weather.

If you still want to wear a heel, consider a lower heel and pump style that offers more support than a stiletto or slingback style.

Save these sandals.

Small Hand Bag

A handbag is a great way to store your belongings as well as to accessorize your outfit. Since you will have to carry it around for most of the day, consider a smaller, lightweight handbag that fits just your essentials.

Wear one of these bags.

Pants Romper

A great alternative to a dress is a pants romper. You will be following the dress code by avoiding shorts, while also looking eloquent and chic. Rompers also come in bright colors and patterns for a bold look. Consider adding a belt around your waist for a more structured look.

Check out these rompers.

Bright Colored Suit

You can have just as much fun creating a memorable look with a suit as with any other outfit. Consider choosing a suit in a bold color or pattern to complement the bright hats and dresses around you. Wear a bright-colored shirt underneath and fun accessories.

Discover these suits.

Necktie or Bowtie

If you are wearing slacks and a sports jacket, a necktie or bowtie is still required for more elite areas. Both are also a great way to add a pop of color or introduce a fun pattern to the rest of your outfit. Think of it as an easy way to accessorize and show off your personality.

See more professional looks here.

Boat Shoes

Boat shoes are comfortable while still being dressy enough to pair with a suit or slacks. They are less stiff and heavy than traditional dress shoes, and offer more personality and style to your look. They look great with no socks or a pair of brightly patterned socks.

Find more dressy shoes here.

Patterned Socks

Fun socks are a great way to add a touch of pattern to an otherwise neutral look or to continue your bold look to the smallest of details. Pattern socks look great with a suit, pants romper, or even a dress. Choose one that compliments your hat, purse, or any other accessories.

Save these socks.

Have Fun With Sunglasses

Sunglasses are a practical piece to bring to shield your eyes from the sun and give you a clear view of the race. This doesn’t mean you can’t have fun with them though. Consider an alternative style with gems, different colors, or a fun shape to wear at the Derby.

Check out these sunglasses.

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About the Author: Shelby Bonner

Shelby Bonner is a freelance graphic designer and writer who is passionate about fashion, and ethical, environmentally friendly fashion. She enjoys finding new brands, and following the latest styles each season.

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