Hats off to the Kentucky Derby

The gracious Churchill Downs

At the iconic Kentucky Derby, it’s unclear whether the hats or the horses command more attention. 

The tote board
The tote board

The Kentucky Derby, which has taken place every year since 1875, is scheduled this year for Saturday, May 3, 2014. For many, it’s a bucket list travel experience.

Often called “the most exciting two minutes in sports,” the race is held at historic Churchill Downs in Louisville, Kentucky and is filled with traditions:

  • Mint Juleps
  • The Rose Blanket
  • The Band Playing “My Old Kentucky Home,” and
  • HATS: All colors, sizes and shapes 
The gracious Churchill Downs
The gracious Churchill Downs

Take a peek at some of the standout hats we saw when we were fortunate to visit the Derby as part of a river cruise stopping in Louisville on the American Queen Steamboat during the boat’s inaugural year:

1) Hats Of All Shapes and Sizes

A little bit of this and that
A little bit of this and that

When it comes to hats for the Derby, there are no set rules—except to wear one or to feel left out. They often have wide brims, feathers, and flowers.

2) Hats That Say Yes to the Dress 

This one says yes to the dress
A perfect match

Many Derby goers select hats to complement their dresses; sometimes the dress complements the hat.

3) Hats That Make a Statement

Sedate by Derby standards
Sedate by Derby standards

Many of the hats, made of silk, satin or organza, are handmade and designed to elicit attention. It takes a certain amount of confidence to wear a hat like this.

4) Hats Are Not for Women Only 


Sometimes that party atmosphere, with plenty of beer, champagne, and bourbon flowing resembles a New Years Eve Mardi Gras.

5) Hats: Win, Place & Show 


Derby goers will go to great lengths to out-do each other with outrageous hats. This one is fashioned of pink flamingoes.

6) Hats For Him and Her 

Matched set
Matched set

Many couples like this one go to great lengths to coordinate their look. This couple finished off the pairing with dark glasses. Her flower matches his bowtie.

7) Last Minute Hats 


These ladies are standing near the pop-up hat shop that surfaced at the historic Seelbach Hilton. The hats on display were designed by Kokin, a hat designer whose boutique is on Lexington Avenue in Manhattan. Some of his handmade designs can cost up to four figures each.

Interested in learning more about Kokin hats, watch this video from the Wall Street Journal:

Tips on Wearing and Choosing a Kentucky Derby Hat

Also on More Time to Travel:
Back on the River: The American Queen Steamboat

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  1. I have written about the Kentucky Derby and I have interviewed the milliner behind Maggie Mae Designs,but I have yet to attend the Kentucky Derby. What a fun post you have written about Kentucky Derby hats!

  2. Hey there! Great Blog! The Kentucky Derby is on my Bucket List for sure.
    I’m just getting my blog off the ground. We have done quite a bit of traveling and have many stories to tell.
    Next on my Bucket List is Liverpool :). Always loved the Beatles and will probably get to London again with a couple of days in Liverpool for sure, maybe sometime this summer.
    I would appreciate some feedback from you on my blog. If you have the time please stop by. My blog of course gets into travel, and also technology. Let me know what you think!

  3. It’s very appropriate that I stumbled across this article after our most recent article was on our experience touring Churchill Downs last weekend (check it out!!). We had an absolute blast there and can only imagine how cool it would be to be there for “Derby Day”. I am familiar with the extravagance of hat wearing at horse races in general because this happens all the time at the races in England, especially Grand National week.

    Great post!

    1. Chris,

      Just visited your blog and loved the virtual opportunity to visit the museum through your narrative and pictures—something I wasn’t able to do on Derby Day!

      Best, Irene

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