Rolling Out

How to pick the perfect hat for the Kentucky Derby

Photo credit: @KentuckyDerby via Instagram
Photo credit: @KentuckyDerby via Instagram

It’s that time of year again, when celebs, socialites and horse-racing lovers alike gather for the annual Kentucky Derby. Kicking off on May 1 and 2, the U.S. Triple Crown series event is expected to draw some of fashion’s biggest fanatics, ready to let their love for over-the-top and outlandish hats shine.


Although choosing the perfect hat can be a bit overwhelming, this headgear tradition first began with Queen Anne and the opening of the Royal Ascot to the general public in 1711, when ladies and gents were required to wear hats in the presence of the Queen. In other words, ponies aren’t the only highlight of the event. As a matter of fact, some would argue that it is one of the biggest fashion events in the world.


Lucky for you, rolling out has put together a few simple guidelines to help you pick the perfect topper for the Kentucky Derby with no stress at all. Scroll below for all the deets.

While there is no hard rule as to what makes a good hat, finishing touches make all the difference. Look for finishes touches that are not only on trend but showcase your unique personality.


By far our most important tip is to make sure your hat fits you properly. The right hat should make you walk tall and feel uber confident.

When shopping for your topper, be sure to bring your outfit with you. This ensures that the pieces will complement with each other.

Size matters! Although the height of your topper depends on the person, it’s all about what you are comfortable wearing. While people have the tendency to think you need to be tall in order to don a big hat, that’s not necessarily true. Go for comfort, a good fit and something you feel good in.

For all you lovely ladies with long hair, wear it tied back for a better fit. Short hair is no problem at all; think about all the hats worn during the 1920s, when many women wore their hair in a pixie cut.

Be sure to have fun when choosing your hat.

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