Best Hats To Wear During Kentucky Derby

I think it is safe to say that there is no other sporting event like the Kentucky Derby in the world. Apart from being a thrilling experience with all of the fastest horses in the world, it is also a fashion runway, a networking opportunity, a way to make some money through betting, and of course a delicious feast.

It is a versatile event where even people who are not horse racing enthusiasts cannot wait for May to come.

There are two most common questions that people ask before they go to the Kentucky Derby.

The first one is, how to pick a winning horse and make some money, and the second one is what to wear on Derby Day.

For the first one, you can check some of the free horse racing tips made by experts on the link below:

And for the second one, you have to educate yourself a little bit more on Derby Fashion.

Remember, this is an event with no strict dress code, but there are certain unwritten rules about what you can and cannot wear on Derby Day.

Like it or not, you’ll be judged on your outfit, and you wouldn’t like to be the one who is underdressed. So, crafting the right outfit is really important. But we aren’t talking about a regular fancy-restaurant outfit, no, no. We are talking about hats, luxury, style, class, and many other things that you wouldn’t normally wear when you go out.

Since hats are quite an important accent to your outfit, we will dive deeper into what are the best hats to wear just so you avoid some of the mistakes that might ruin your day.

History of Kentucky Derby Hats

The Kentucky Derby wasn’t born as a fashionable event. In fact, at its beginnings, everyone showed up on the track in whatever outfit they wanted. However, as horse racing events started to become social gatherings where people were showing off their status and wealth, hats became a symbol of higher society.

Over time hats evolved into a fashion trend, with attendees competing to wear the most eye-catching and unique hat designs.

Types of Derby Hats

When we talk about hats, there are certain rules and specific styles you’d want to wear. You cannot show up on the Kentucky Derby with a baseball hat. Here are some of the best choices:

Wide-Brimmed Fascinator: These iconic Derby hats have wide brims decorated with feathers, flowers, and ribbons. They ooze elegance and class, ideal for making a statement at the racetrack.

Fascinators: Fascinators are a trendy accessory for a more contemporary and whimsical style. These tiny, ornamental headpieces frequently contain complex patterns with feathers, pearls, and netting, bringing a bit of whimsy to your Derby look.

Fedora Finesse: Fedora hats have made a stunning appearance in women’s Derby wear. Fedoras, with their structured brims and ageless appeal, offers a retro touch to any ensemble.

Pillbox Perfection: Wear a trendy pillbox hat to channel your inner Jackie O. These sleek and classy hats lay atop the head, providing a comfortable but fashionable option for a day at the races.

Choosing the Perfect Hat

In order to find out which is the best hat for you, there are certain rules you need to follow. The ultimate guide is to wear a heat that you’ll feel confident in and that matches your style and character.

  • Match Your Outfit: Your hat is the most noticeable accessory in your outfit, so make sure the colors, textures, and style go along with your overall outfit. You wouldn’t want to choose a hat that feels like doesn’t belong in your outfit.
  • Consider Your Face Shape: Just because someone else is rocking a certain style of hat, doesn’t mean that you can wear the same. Hats accent your face differently, and that’s because of your face shape. Make sure to try a couple of different styles and see which one works best for you.
  • Make a Statement: As we mentioned before, hats are the ultimate accessory if you want to stand out from the crowd. On top of that, they are a perfect way to express yourself and your fashion. So, don’t be afraid to go BOLD! There are many ladies that create their own DIY hats that include horse accessories, or something that highlights their personality.

Fun Facts About Derby Hats

The average weight of a Derby hat is around 8-10 ounces, but some extravagant designs can weigh up to a pound or more!

The Derby hats can be quite expensive. A custom exclusive hat will cost you anywhere from $400 to a whopping $2,000 depending on the materials used.

Each year, the Kentucky Derby attracts thousands of hat enthusiasts who compete in contests such as the “Most Creative Hat” and “Best Vintage Hat.”


Q: Can men wear hats to the Kentucky Derby?

A: Absolutely! While women’s hats often steal the spotlight, men can rock stylish fedoras, bowler hats, or even top hats to complement their Derby attire.

Q: Are there any rules or etiquette for wearing Derby hats?

A: While there are no strict rules, it’s customary to remove your hat during the singing of “My Old Kentucky Home” as a sign of respect. Also, try not to obstruct someone’s view of the race with your huge hat.

Q: How do I secure a large hat on a windy Derby day? A: Use hat pins or discreetly attach small weights inside the hat to prevent it from flying away in the breeze.

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