Kentucky Derby Hats: The History Behind the Fashion

A few years ago my friends and I went on a girls’ trip to the Kentucky Derby. During the race, there was a crazy woman standing in the infield screaming “You’re all winners!!!” at the horses as they sped around the track. That crazy woman was me.

Truth be told, I don’t care for horse racing or any sport that exploits animals for entertainment. And while I’m not a fan of the Kentucky Derby itself (too many horses dying) – I do love the fashion. In fact, I think they should do away with the horse race altogether and just make it one big drunken fashion show where everyone struts around the track in their best hats!

It rained when we attended the Derby in 2019, so our hats were not just fashion statements. They protected us from a very bad hair day. As you can tell from the photos below, the rain certainly didn’t stop us from having a blast. Or maybe we’d just had one too many mint juleps.

As a vintage collector, curator, and seller, I wanted to understand the history of the Derby hat and how it became such an iconic fashion statement. So I went straight to the Kentucky Derby’s official site, which provided most of the details and photos for my research.

Here’s what I found.

Kentucky Derby hat styles through the decades

The 1870s

The first Kentucky Derby took place in 1875. This was the beginning of the “gilded age” in fashion.

The wide-brimmed and elaborately styled hats worn at the inaugural race would have been constructed of straw with satin and velvet trim and decorated with feathers.

The 1900s

In the decades that followed the first run for the roses, fashion became more streamlined and simple.

Kentucky Derby hats for women retained their wide brims and satin ribbons, but the extravagant plumes and feathers were absent.

The 1920s

The roaring 20s introduced “flapper” style and the popular bell-shaped cloche hat. (Cloche being the French word for “bell.”)

With its simple design and low brim, the cloche was definitely the most understated style of hats in Kentucky Derby fashion history.

The 1930s

Hats remained small in the 1930s, but the brim was lifted and many were worn tilted at an angle, paving the way for the popular pillbox styles.

Plumes and feathers returned as did wide satin and velvet ribbon trims.

The 1940s

In the 1940s, turbans and snoods became popular as the original “bad hair day” coverup during wartime, when women were working in the factories and money for regular hair appointments was tight.

Certain materials like felt and straw were scarce, so trimmings such as flowers, ribbons, feathers, and netting were used in greater quantities to construct larger-looking hats that influenced Kentucky Derby style in the late 40s.

The 1950s

Post World War II, the fashion industry longed for a return to glamour.

When Christian Dior launched his “New Look” collection in the late 40s, saucer and cartwheel hats became as popular as the new look itself, as they were quite complementary to the wider style skirts and dresses.

The 1960s

Wider brimmed hats became popular again in the 60s thanks to the floppy styles worn by the hippies and beatnik generation.

Whether adorned with a bouquet of flowers or a single satin bow, these Derby hats were a throwback to the original 1800s versions.

The 1970s

Both the hems on the pants and the brims on the hats got wider in the 70s.

Floppy hats continued to be popular throughout the decade, appearing at the Derby with wide brims and wide trims in satin and silk fabrics.

The 1980s

The only thing that got smaller in the 1980s when it comes to fashion were the hats.

While big shoulder pads and big hair were the trends of the decade, it was just the bright neon colors of the 80s that made it into the overall hat designs.

The 1990s

When I think of hat styles in the 1990s, I think of Julia Roberts in Pretty Woman and I also think of Princess Diana.

The hats of the 90s were definitely a flashback to the wider brims and more elegant styles of the 1950s and 60s.

The 2000s

Reality stars descended on the Derby during the 2000s, bringing much more attention to the fashion and the race itself.

While the clothing got smaller and the waistlines dropped lower, the hats definitely got bigger and brighter.

The 2010s

Okay, so my best friend Missy and I got in at the very end of the decade here in 2019.

The royal wedding of Prince William and Kate Middleton in 2011 made the fascinator hat fascinating again. I actually ordered this hat from Amazon and Missy wore this beautiful cream and black hat from my vintage shop.

So while Derby hats have changed throughout the decades, there are two things about Derby style that remain the same: creativity and individuality. My advice for dressing for any outdoor formal event is to start with the hat and build your entire look around it. Start at the top and the rest of the look will follow.

And let’s hope they either find a way to make horse-racing 100% safe and beneficial for the horses, or do away with it altogether. Fashion is fun. Animal abuse is abhorrent.

Check out some of the vintage hats available at Shop Stylaphile

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