Attending the Kentucky Derby in Style

For much of the Kentucky Derby — and the sister event, the Kentucky Oaks — the spotlight is on the horses … or is it? If the greatest two minutes in horse racing history occupy only a small fraction of the length of the event, what is everyone doing for the rest of the time?

Sure, there is speculation, betting, and inspecting — but most people are thoroughly enjoying their people watching. Whether you are watching or being watched, you want to stand out in the crowd and attend the event in extravagant, appropriate style. The easiest way to go to the Kentucky Derby is to book a luxury package through Superior Executive Services. Stand out and stand above the rest with Superior Executive Services.


We explored the tradition of wearing large hats in a previous blog. Just for a recap, the hats became a method of gentrifying the Churchill Downs, courtesy of the founder, Meriwether Lewis Clark, Jr. Soon, the big hats became a way people could stand out in the crowd and be noticed.

One interesting approach to standing out amongst the flamboyant hats is to wear a small, boldly decorated fascinator. While most women wear wide-brimmed, gaudy hats, some are choosing fascinators as a way to stand out with an entirely new style. These fascinators include netting and sometimes flowers that compliment the colors on a dress.

For men, fedoras and bowler hats have always been a popular choice. While some are partial to a clean-cut razor fade, others prefer hats. There is also the option to wear a Derby hat, usually sold in color, taking inspiration from the style of the ’20s.


This can be a contentious subject. When you attend the Kentucky Derby, you will see every single color you thought existed painted onto pants, blazers, hats, shoes, and handbags. There are a few very important things to remember when dressing this boldly.

Be careful when mixing patterns. Different plaid patterns are okay, but sometimes when folks wear a seersucker suit with a plaid vest, it can be a bit much. Wearing more than two or three different patterns can look busy and tasteless. Stick to like patterns and don’t be afraid to proud to wear stripes or a modest herringbone.

Research your complimentary colors. Take some time to think about which loud, screaming colors work best in tandem. The quickest way to root out an unfashionable person is seeing too many uncomplimentary colors in their outfit.

Blazers should be elegant. Whether you’re sporting a masculine or feminine look, your blazer should not be the craziest part of your outfit. Some folks wear blazers with a rose graphic on it or pink and green flannel. The blazer is what brings everything together, simply complementing the rest of the ensemble.


The most important thing to remember is to sport a positive attitude. If you feel good, you look good. If you don’t think you’ll feel comfortable sporting a giant derby hat, don’t go for it. Same goes for those brash prints.

The goal of the Kentucky Derby, as a spectator is to have fun. Be sure to enjoy all the people watching and high-fashion this year by booking a luxury derby package through Superior Executive Services. We offer some of the best services to provide you with an unforgettable experience. So, ladies and gentlemen, place your bets and visit our website to book a trip today.

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