Kentucky Derby Hat Hairstyles

The Kentucky Derby is known as “The Most Exciting Two Minutes In Sports” in the United States. These two minutes of fun call for endless hours of celebration. When attending the Kentucky Derby, it’s the perfect opportunity to sport your finest Southern Belle attire.


What separates the Kentucky Derby from every other event? The hats! There are no rules when choosing your hat for the derby, from flowers and ribbons to straws and plastic cups – you can do it all. But, we’re here to help you navigate the hairstyle that you should wear with your eccentric or classic hat at the Kentucky Derby – or for any event that allows you to wear a fun and funky hat.


Side Chignon with Fascinator Hat

The fascinator is a more recent trend – thanks to the lovely Kate Middleton. This hat is smaller than a traditional derby hat but just as stylish. These chic headpieces can look lovely with a variety of styles but we think a side chignon is the perfect classic compliment to this headpiece. Side-swept bangs with the side-chignon complete the face-framing look.


Side chignon for Kentucky Derby

Long Side-Ponytail with Floppy Hat

Kentucky in May can be hot – or humid – or hot & humid. A side-ponytail is the perfect option for a big floppy hat because you can still show off your long hair and wavy texture but it keeps your hair controlled under the hat – and off your neck for the unpredictable Louisville weather.


Side-ponytail with floppy hat

Tucked Under Updo

These big hats can create a sense of mystery as to who is hiding under the big rim and big style of the derby hats. Having your hair tucked up only adds to the allure of the mystery while passer-by’s try to sneak a look. Keep your hair sleek and tucked under the big hat, only reveal a few inches of a bun or curled up-do.


Classic Kentucky Derby look


Updo for the Kentucky Derby

Straight Bob with Big Fascinator

If you have a bob, the big hats can seem too overwhelming some times. Rather than a hat, opt for a big, statement making fascinator. It will perfectly compliment your fine chin-length bob.


Simple Southern Belle hat and hair

Steam-Punk Hatter Hats with Wavy Bob

If you’re opting to wear the mad-hatter style look rather than a floppy hat or fascinator, mad hair is the perfect style. Undone texture like messy waves or a choppy bob look will give your Southern Belle style an edgy twist.


Mad hatter derby hat

Luscious Long Waves

These big hats often call for big hair too. If you’ve got longer locks, heat up your curling iron and don’t be afraid of big waves or curls. It’s the perfect Southern Belle look to compliment the big floppy hats with tulle and feathers.