Kentucky Derby Hats

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A Kentucky Derby hat is a small-brim hat that is often made from felt and features a rounded top, with a brim that wraps around the entire crown and tilts up at the sides.


A Brief History of Kentucky Derby Hats

The hats were first made in the 1850s by the Bowler Brothers, who were commissioned to create headwear that would protect polo players’ heads from tree branches. At that time, the hats were known as bowler hats after the brothers that created them.

Eventually, the bowler hat made its way to Europe and was loved by clerks, bankers, and the like. When the bowler hat arrived in the United States, it replaced the cowboy hat and sombrero due to its close-fitting construction that wouldn’t budge even in strong winds. It was also popular among outlaws like Billy the Kid and Black Bart.

Kentucky Derby Hat vs. Bowler Hat: What’s the Difference?

So, why is it called the bowler hat in the U.K. but the Kentucky Derby hat in the U.S.? In 1780, the Earl of Derby set up a horse race called the Epsom Derby. When the bowler hats were introduced in the 1850s, dapper men started to wear them to the derby, as the hats had the ability to stay put, and wouldn’t get blown into the field. As bowler hats grew in popularity among the working class, and as more gentlemen wore them to the races, they were soon nicknamed “derby hats”.

When the headwear made its way to the U.S., men already dubbed it as a derby hat. Since the U.S. has its own derby called the Kentucky Derby, men tweaked the name and turned it into the Kentucky Derby hat.

If you’re looking for a Kentucky Derby Hat, don’t be surprised to see brands selling it as a bowler hat. The two are synonymous.

The Anatomy of a Kentucky Derby Hat

Kentucky Derby hats were first made from fur felt that was spun together to create a tight, waterproof surface. It has a low and narrow crown that’s designed to tightly wrap around the head, as well as a hard brim that turns upward at the sides. Some Kentucky Derby hats are also lined with silk and coated with shellac to help keep their shape.

Why are Kentucky Derby Hats So Popular?

The Kentucky Derby is a horse race that’s held in Louisville, Kentucky every year. It marks the end of the fourteen-day-long Kentucky Derby Festival.

Over the years, the Kentucky Derby has evolved into a more fashionable event than a mere spectator sport. Now, its spectacle is more than the race, but the derby hats that are worn by its world-famous guests such as Shailene Woodley, Tom Brady, and Aaron Rodgers. People worldwide tune into the Kentucky Derby to look at the attendees’ derby hats.

Kentucky Derby fashion now embraces all kinds of headwear, such as wide-brim hats, straw hats, and summer hats, but the Kentucky Derby hat shape is still the most timeless option.

Do keep in mind that the Kentucky Derby is the time to wear a one-of-a-kind hat, so be sure to buy one that isn’t too basic. Some men like to adorn their Kentucky Derby hats with ribbons in order to stand out. You could also buy a derby hat that’s already embellished, like the Godfather Hat or the Rocco Hat by Bruno Capelo.

Where Should You Wear a Kentucky Derby Hat?

Even if you aren’t a fan of the Kentucky Derby, you can still don a Kentucky Derby hat with everyday wear. The key is to wear the Kentucky Derby hat with formal and semi-formal ensembles. Whenever you wear a suit or vest, wear a bowler hat or Kentucky Derby hat to look more put-together. If you want to go full-on “Charlie Chaplin”, pair the bowler hat with a bowtie that’s made of the same material.

What to Wear With a Kentucky Derby Hat

Kentucky Derby hats or bowler hats are best worn with semi-formal and formal attires. For an effortlessly classic look, wear your bowler hat with a stroller suit, Stresemann suit, or business suit. For a laid-back (but still debonair) look, the options are endless, but it’s best to stick with “hipster” wear like vests and button-downs.

How to Wear a Kentucky Derby Hat

The Kentucky Derby hat is supposed to sit flat on top of your head. It should not lean to one side. It is designed to snugly “hug” the head, so if it starts to tilt as you walk, you’re likely wearing the wrong Kentucky Derby hat. It should never budge even with the slightest movement.

Find the best Men’s Kentucky Derby Hats at DapperFam

Whether you’ve been an avid fan of Kentucky Derby fashion for ages, or if you’re finally going to the grandstand as a guest, we have a wide selection of Kentucky Derby hats for one of the United States’ most popular (and fanciest) sports. At DapperFam, you’re sure to find the perfect derby hat that a true gentleman such as yourself should wear.