By: Danielle Rudy Davis

The Kentucky Derby is an event unlike any other and that extends from the Most Exciting Two Minutes in Sports®all the way to the unmatched style. Derby week is a chance to show up and show out with men and ladies pulling out all the stops. For some that might mean bold, bright, floral looks and for others it’s a chance to showcase a refined elegance. But the same rule goes for everyone in attendance: dress to impress.

The Dress

When it comes to picking the perfect Derby Day look, the biggest thing to keep in mind is where you’ll be sitting and what section of Churchill Downs you’ll be taking in the races from. If you’re sitting in an outdoor box, you’ll want something that is chic, fashionable and easy to wear for a day in the sun. The Vineyard Vines Kentucky Derby collection, with its mix of floral print cotton, flirty eyelet and smocked dresses are perfect for a sunny, spring day.

The higher up you go in the clubhouse, the dressier the attire. Plan on seeing gorgeous dresses at every turn paired with fascinators and hats to match. Some areas also have specific dress codes, so don’t forget to check before choosing your dress or outfit.

Derby Fashion isn’t just for the ladies. Bright sport coats, slim fit suits, pastels, seersucker prints and more can be seen through the track. Coordinate with your date or make a solo style statement. Either way, this isn’t a time to be simple.

The Hat

You can’t come to Derby without a hat or fascinator. Well, you can, but where’s the fun in that? The Kentucky Derby is known for its sea of hats.

In the last decade, we’ve seen more ladies opt for fascinators but you’ll still see a wide mix of options. While some opt for feathers and florals, others choose more structured, sculptural pieces - similar to what you see on British royals. When choosing a hat, make sure it’s something you’ll feel comfortable wearing all day. While the Kentucky Derby race only be two minutes, the day is a marathon.

No matter where you’re sitting, you’ll want to make sure to top off your look with an eye-catching headpiece. Need some inspiration? Featured Kentucky Derby Milliners The Hat Girls, Christine Moore and Forme Millinery handcraft pieces that can make any outfit a showstopper. And the hats aren’t just for the ladies, the guys get in on the action with a mix of sleek fedoras, Panama-style straw hats, boater hats - like this one from Vineyard Vines - and more.

The Bag

The finishing touch to every look, your bag is a very important part of your Derby ensemble. First off, you’ll want to make sure it meets Churchill Downs’ bag policy. One way to avoid issues while looking chic and stylish is to order one of the gorgeous Radley London x Kentucky Derby bags. The collection features equestrian accents like horsebit clasps and hardware, rose details in a nod to the garland of roses for the winner and beautiful leather detailing.

The bags are the epitome of fashion meets function and the classic colors mean there’s an option to pair with whatever you’re wearing.

Be totally Derby ready by packing a pen for jotting down your picks, an extra ponytail holder or bobby pins for windy day hair emergencies, toss in a couple bandaids in case of blisters and bring your lipstick for any touch ups.

The most important tip is, of course, to have fun with your outfit. Style at the Kentucky Derby is all about expressing your personality and individuality with a splash of spring. See you at the races!

Follow us for the latest news, updates, and contests:
Privacy Policy
Thank you to our sponsor