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Kentucky Derby Hat Guide

The Kentucky is here. Luckily, you don’t need to travel to Kentucky to actually experience the festivities. Lots of people host watch parties in their homes and allow guests to dress stylishly. What if you get an invitation to one of these parties and are in desperate need of a hat? What is a Kentucky Derby Hat anyway?

Unfortunately, women have a more difficult time of selecting the proper hat. If you’re onsite watching the race, many women wear gigantic flamboyant hats. For those socialites, it’s important to wear a unique hat that no other lady will be wearing. It’s a competition, of sorts, perhaps with more stakes than the race itself.

Luckily though, if you’re staying local and going to your friend’s barbeque, you don’t have to spend $1,000 on a signature designer hat. You can if you want to, but you’ll probably be better suited with something else.

Women’s Kentucky Derby Hats

There are two main options for a women’s hat. Your choices are big floppy hats or tiny fascinators. You could wear whatever you wish, there are no hard rules governing the correct head coverings. The feeling we’re going for, however, is to copy what we see on TV.

There are many other types of hats which look appealing on women, which could pass as a nice attempt. A cloche hat or a Bretton come to mind. They’re perfectly wonderful hats, and you should just wear it if it makes you feel confident. In general, if you’re going to steer away from the trend, make sure what you select has a bow or flower on it, as that’s the real Derby style.

Also, women can go against the grain entirely and wear a hat better suited for a man. Imagine wearing a fedora to a Kentucky Derby party. It’s a perfectly appropriate hat, but more of a tongue-in-cheek sort of way.

Primarily, stick with the wide brimmed hats and fascinators. We’ll look at some styles here:

Kentucky derby hat for women
Wide Brimmed Cap

This Jeanne Simmons Wide Brimmed Hat is a perfect choice. You want your Kentucky Derby Hat to have flowers or a bow, and this one has the big ruffle bow hanging on the side. It’s lovely.

Some wide brimmed hats are better suited for the beach, so you need to be careful how relaxed of a feeling the hat gives. You want to pick more of a formal hat, almost like a church hat or an Easter hat. But there are plenty of trendy straw hats for women, that aren’t necessary vacation hats, so this rule is more of a guideline.

Fascinator Cap
Fascinator Hat on Dummy Doll

A much simpler and elegant route is to choose a Fascinator Hat. Fascinators give you the freedom to move about, whereas the wide brimmed hats are cumbersome and awkward. This Jeanne Simmons fascinator is a great choice with netting and bow. Other versions may come with flowers to stay in the horse racing theme.

Men’s Kentucky Derby Hats

This is the one time a year when men can wear fun hats and receive praise for it. For the Kentucky Derby, men get the option of a boater hat, bowler hat, or a fedora.

As with women’s hats, there’s no steadfast rule to stick by. You could wear a top hat if you wanted to, but you’ll probably be the only person wearing one. Similarly, you could wear a baseball hat. Like literally, you could physically walk into the Kentucky Derby wearing a baseball hat, but people might think you were insane. You really should not do that. A baseball hat is much too informal a headpiece.

Boater Hat
Kentucky Derby Hat for Men

The Boater Hat is an old-timey hat no one wears anymore, but whip it out on Kentucky Derby Saturday and you’ll be a hero. A hundred years ago men used to wear these as regular everyday summer hats. We sort of wish they were still popular. It’s a cool hat.

Bowler Hat
Bowler Cap for Men

Another timeless classic for men is the Bowler Hat. Also appropriately called a derby hat, this hard round crown was originally used by men on horseback while hunting game. The relationship still exists between horse and men that this hat makes a stunning impression at the races.

Fedora Hat
Stylish Fedora Ha

Our favorite choice for a stylish Kentucky Derby Hat is the fedora. A fedora will look nice on a normal day, but on race day they’re elevated to a whole new class of fashion. Fedoras also come in warmer wool varieties, but we recommend a Straw Fedora Hat for that springtime race.

If you’re really trying to dress up and look like a real gentleman on Kentucky Derby Saturday, a fedora is a way to go. The other hat options are perfectly fine, but a fedora is the best and will work well with lots of face shapes and outfits.

Well, that’s it for now. We hope you’re able to learn from these tips and enjoy the race with your new hat.

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3 Comments

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