Famous Horse Racing Hats You May Have Never Seen

Grab a mint julep, and let’s head down memory lane for some of the most famous horse racing hats to have graced race tracks and some history.

The bigger, the better, whether at the Kentucky Derby in Louisville or the Royal Ascot race in England, the hats adorned at these races make it much better.

So, From paper mache hats to hats filled with awards, showing up to horse races requires bravery, grace, and a little creativity.

Famous Horse Races 

Besides the Kentucky Derby, several horse races worldwide have seen incredible hats and had royal attendees.

  • The Preakness Stakes in Baltimore, Maryland
  • Belmont Stakes which happens in Elmont, New York. Prix
  • Prix de l’Arc de Triomphe takes place in Paris, France
  • The Royal Ascot at Berkshire Ascot, England
  • Dubai World Cup in Dubai, United Arab Emirates
  • The Grand National always happens in Aintree, England
  • Melbourne Cup happens in Melbourne, Australia
  • Nakayama Grand Jump in Funabashi, Japan
  • Kentucky Oaks goes down at Churchill Downs 

History Of Horse Racing Hats 

A familiar spectacle at horse races, such as the Kentucky Derby and the Royal Ascot, is men and women and sometimes dogs, sporting tremendous, stylish, and at times flashy hats along the tracks with all sorts of embellishments. Horses and horse racing have been around for thousands of years. 

While the same can’t be said for the hats usually worn at these events, whether you’re a horse fanatic or a lover of all things fashion plus horses, heading down to a race is mainly followed closely by the entertainment from watching the hat catwalk.

From the royals being spotted out during the Royal Ascot wearing the most stylish fascinators or celebrities and hat enthusiasts at the Kentucky Derby adorning hats filled with a hundred red roses, there’s no shortage of that goodness at a race track. 

However, the tradition of wearing hats to US races can be traced back to 1875. This adorning of hats was when women dressed, and their crowning jewel was the hat.

Also, this long-standing tradition was started by Colonel Meriwether Lewis Clark Jr and is a mix of British and Southern cultures. 

Case In Point – The Kentucky Derby

This derby is one of the most famous horse races in the world and is held at Lousiville Churchill Downs on the first Saturday of May every year.

Therefore, horse racing is most famous for the incredible hats on display, with the women gracing the tracks tailoring their hats depending on where they are seated.

The attending party within the general infield area of Churchill Downs tends to wear more eccentric hats.

Generally, these hats come in all shapes, colors, and sizes, with some emanating the wearer’s personality and humor.

Some past attendees’ hats were replicas of Churchill Downs, complete with motorized horses. However, others were stuck on as many miniature liquor bottles as humanly possible. 

While the guests within the seated areas of Churchill Downs edge toward elegance and style, some women in attendance tend to lean towards the southern belle-inspired hats despite the differences.

In contrast, others let out their creativity, which makes the races such as ball. The hats seem to come with a combination of flowers, feathers, ribbons, and bows. 

Why Are Hats Worn At The Races? 

As a long-standing tradition that dates back years, women who attended races wore hats as a status symbol. The hats were a fashion statement and status symbol for those participating in the races.

The ownership, maintenance, and sport of horses were inherently expensive and, as such, were closed off to those who weren’t as well off. 

The men would “invest “in their wives to show their wealth. They ensured that their women were dressed in the finest and latest fashion trends.

Jump to now, and the tradition continues to live on throughout the racing scene worldwide.

Long Live The Tradition 

A tradition that has continued to this day, wearing hats to the races is considered to bring good luck. And the bigger the hat, the more considerable luck.

Women started the tradition. However, in the last couple of years, men have joined in honoring the tradition and indulging in the fun.

Wearing a hat is considerably similar to getting into costume. You never know what type of character you might turn out to be.

Possibly the most famous horse race in the world, the tradition of wearing large-brimmed and, at times more miniature, brimmed hats dates back to the very beginning of the Kentucky Derby. 

What Type Of Race Hats Do Men Wear? 

With the women leaning more toward southern Belle-inspired hats, the men have various options that are much less labor-intensive. At the tracks, they can be seen wearing multiple hats, such as: 

The Trilby 

According to the Jockey club, the Trilby is shaped like a shortened angular fedora. 

The Panama Hat 

The Panama hat is similar to the fedora and the Trilby. However, the Panama hat is created by weaving palm trees or straw as an alternative to felt. 

The Top Hat 

Quite possibly the most famous hat worldwide, the Top hat is a crowd favorite among men and magicians. The Top hat goes with the Morning dress on Derby Day.

The Flat Cap 

The flat cap is a round cap with a tiny hard brim in the front. It’s made from wool, tweed, and cotton.

The Baker Boy 

One of the more casual hats, the Baker boy, is more similar to the flat cap with the same shape and stiff peak. However, it has a rounder, fuller, and paneled body.

What Do Women Wear At These Racing Events? 

Other than the quintessential southern Belle-inspired hats, women can also wear the fedora, Trilby, Panama, Baker Boy, and Flat cap. Additionally, they can adorn the following hats: 

The Boater Hat 

When people think of British social events, the guests are almost always considered to be wearing boater hats. The hat is fashioned from stiff sisal straw and finished with a bright ribbon.

The Pill Box 

The pill box is small with a flat crown, straight, upright sides, and no brim. It got its name from the small cases of pills that used to come in. 


Fascinators is one of the more affluent hats on this list. The modern-day fascinator is a traditional headpiece molded and shaped by fabric at the base and is usually worn at British events (formal ones).

They can be large or small, worn on either side of the head, decorated with anything from feathers and beads, and attached to a headband, hairclip, or comb.

Style Tips 

Here are a few style tips to help you choose your next headpiece for the next round of the sport of kings. 

  • Consider wearing hats with a wide brim and shorter crown if you’re tall. These types of hats tend to be the most flattering. 
  • Select hats with a low profile crown and small brim if you’re on the shorter, petite side. Fascinators with a little bit of height in them can also work these work best and tend not to overpower your figure. 
  • If you’re curvy, full-brimmed hats tend to work best.
  • If you have short hair, choosing a flip-brim hat or a fascinator works best to show off the face and hair. 


The are several influences that went into the formation of the Kentucky Derby. Colonel Meriwether chose to model the Kentucky Derby after British and french horseracing. Before fans sang along to “Kentucky, my old home.” 

During one of his European trips, he attended the Epsom Derby in England. Through inspiration from his travels, he determined to create a race of the same caliber in the United States. 

How To Shop For A Racing Hat 

Attending a horse race requires the right accessory. While the Kentucky Derby offers guidelines for how to dress, getting the right accessory during the most exciting two minutes of a sport can make or break your outfit and experience. 

Depending on your dress’s color and stature, you can either go the traditional way of wearing the enormous budget that you can lay your hands on or the fascinator way, a more lightweight headpiece that fits on the head thanks to an elastic band.  

The price range for a derby hat ranges from a couple of hundred dollars up to a couple of thousand dollars, and this is all dependent on the milliner you decide to go with.

Shelling out hundreds of dollars doesn’t dictate the type of experience. However, customizing your hat with things on hand is also a creative way to keep the sun away from your eyes and still partake in the tradition of mint juleps, people-watching, and horse-watching. 


The tradition of wearing Derby hats has been around for ages and will hopefully continue to live on. Thus, whether you go bright red for the tradition or take a more subtle approach, there’s no feeling quite like it.