Project Description

What to Wear to the Races??

Kentucky Derby Hats

Whether you’re off to Ascot, the Kentucky Derby, Saratoga or Le Prix Diane, it’s about more than the horses.  Going to the races is an opportunity to exhibit some race day fashion.  But what should you wear to the races?

It will depend upon which race.  Are you going to the Kentucky Derby?  Perhaps Royal Ascot Ladies Day is more your thing.  Is Dubai your destination? Regardless of which location, think elegant, stylish and comfortable. Then find the right hat.  One that makes you feel fabulous and is a reflection of your personality.  Many women love wide brimmed hats for the races and I’m happy to say that almost anyone can wear a wide brimmed hat. Proportion is the key.  If you’re looking at Kentucky Derby hats that are wide brimmed, the hat should not extend past the width of your shoulders. You don’t need a measuring tape, use your eye to follow the rule of thumb.

Race day fashion requires some planning.  Some prefer to select a race day outfit and then go searching for an elegant hat, while others find the fabulous hat first, and then work on the ensemble. Both strategies work well.  As a milliner, I’ve had clients come in with a picture of their race day fashion and ask me to design a hat in keeping with the affair.  While other clients have given me carte blanche to create a statement piece and then found the right outfit.  If the chapeau is over the top, I recommend keeping the outfit simple.  Similarly, if the ensemble is striking then the hat should be more of an accent piece.

So there you have it, some race day fashion advice for the Kentucky Derby or any other race you plan on attending.

kentucky derby hat
black and white race day hat

Just a few of the Kentucky Derby hats that we’ve made for clients

How to decide on the perfect Kentucky Derby Hat

The Kentucky Derby happens once a year in Louisville, Kentucky. The event has been taking place since 1875, on the first Saturday in May.  If you’re so lucky to be viewing the race from a box seat, it’s well worth taking the time to plan your outfit.  After all, when else do you have the occasion to wear a fabulous racing hat?

As a milliner who has made many racing hats worn at the Kentucky Derby, I’d say that there are two ways to start planning your outfit:

with the hat or

with the outfit

If you start with the hat, it means that you find the hat first, and then plan your outfit around the hat.  Your dress, shoes, handbag and other accessories are only selected post hat.  You’ll want to start with the hat and then coordinate the rest.  I say coordinate because matchy-matchy is no longer an approved fashion choice. A good rule of thumb is the more elaborate your hat, the simpler the outfit.  You don’t want the two competing.

If you start with the outfit then you might need to work with a milliner to find the right color and tone for your hat.  Machine made hats come in standard colors: black, white, beige or navy.  Traditional milliners know how to dye fabrics, straw, feathers, and other elements to achieve the perfect tone for your outfit.

Give yourself 3 months to get ready so you have plenty of time to shop and find exactly what you need.

The race started in the Victorian Era and the event still conjures up images of women wearing huge hats.

But that was then and this is now.

Take my advice and keep the hat size in mind if you are traveling to Churchill Downs by airplane.  Unless you are flying on your private jet, airlines have become quite restrictive in what can be carried on.  Many hat boxes don’t fit in the overhead bin.  Placing them under the seat only works if you don’t need leg room.

Of course, if you absolutely, positively must have a fabulously large racing hat for the Kentucky Derby consider mailing it ahead.

Wide Brim Fun

Kentucky Derby Hat