Everytime I wear a hat I get compliments. If you read my “Hello” page you know that I Love Hats. I have several for the winter that are felt with ribbons, a feather or a flower. Summer brings out lots of variation in wide brims that provide shade to my face.
Welcome to my second in the Kentucky Derby Series! If you missed the first one you can check it out at Kentucky Derby Party Planning.

One of my favorites. Bought it and the coat at White House Black Market during a visit to California to see my best friend about 6 years ago.
In the 1800s it was considered proper etiquette for a man or a woman to don a hat if they left their home for any reason. If you enjoyed the recent popular series “Downton Abbey” you would have been exposed to gorgeous hat designs. But you also would note that even the servant class wore hats when out in public, just a less showing or elaborate one. Notice the more muted colors of the early 1900s verses even my little Red Hat and of course the very often Bright colors of today’s Derby Hats.
When Meriweather Lewis Clark, Jr. got inspired to bring sophistication to a sketchy track sport here in the USA, he found that inspiration in Paris and England. He brought his plan back to his family the “Churchills” and convinced them that the races they were holding at Churchhill Downs could draw a different crowd.
They went on a campaign door to door, social club to social club and told the socialites there would be a picnic at the Derby on May 17. So in 1875, 10,000 people met for the first ever Kentucky Derby on the grounds of Churchill Downs. They came dressed in their fine clothes and of course hats, both men and women. It was the place to be seen.
Over time there have been lulls and valleys over the fashion but in the 1960s when television began airing some of the races, fashion and hats again took their place as the focus sometimes over the horses and riders.
To attend the Kentucky Derby without a Hat is considered bad luck and bad form. Socialites begin ordering their hats from New York and Paris in February ranging from $300 to $2000. While others buy off the rack or take a simple straw hat or fascinator and decorate it themselves. There is no snobbery here. Every hat is a contender and every color and amount of creativity is welcome and encouraged.
Some say you buy the hat and then find your dress. I agree. Having ordered what I was told was a “pink” hat on line, I started the shopping for my dress but had not found one by the time the hat arrived. I had found my husband a beautiful orange and white with a touch of soft blue shirt and a bow tie that went great with it. Little did I know he was into the fashion and was already looking on his own. At that point I wished I had ordered coral since it is my color and would look much better with him in his orange. The next day my hat arrived and it is much more coral than it is pink!
Also note that the HAT is the star, not your dress or slacks or jewelry. All other fashion is worn to complement and showcase your hat.
In the midst of writing this post I found a dress. The lighter color in the dress was an exact match to my hat and the dress also had black and a little of the bright orange in my husband’s banding. I loved it! I found a belt and added a orange flower to it and just thought how cute with my little black slipper shoes…until I tried on my hat. Guess what? I allowed my dress to take the spot light and the hat just didn’t look right with it at all. So it is true…let the hat do the talking!
So what kind of hat does a woman wear to the Kentucky Derby? The choice is yours but typically the most popular is the wide brimmed straw hat in color with lots of lovely trimmings.
To purchase online there are too many places to mention but I will give you a few suggestions. I bought mine on Amazon.com. It was $34. I thought that was a very reasonable price for a hat that I was thrilled to wear without changing or adding a thing. Honestly when you start hot gluing ribbons, flowers, netting, etc., those items will start adding up and a simple hat can run you $25 easy and you may not be happy with it in the end.
Another type of hat that has become popular since the wedding of Kate Middleton and Prince William, is the Fascinator, although I have recently learned that in truth a Fascinator is a headscarf and the true name of this style hat is a “Whimsey.” It is a small little circle of straw held on with a headband. From this little circle some of the most fabulous hats have been built. Typically worn to one side it is a flattering style on any lady and leaves hair looking wonderful after the hat is removed.
You can find Fascinators or Whimseys at many places as well. But again I have to give Amazon.com the Best Value award. Lots of variety and color for a very smart price.
What type of hats do men wear? The most interesting thing I found in my research is Men have an array of choices that are truly different when it comes to Hats suitable for the Kentucky Derby…far more than women in fact. The Official Hat of the Kentucky Derby is the Fedora. A short brimmed hat. The color of the hat can be different, the band can be different and of course if you decorate it out or have it made to your specifications, well, you can have a very full brimmed and outlandish hat even as a man.
When the Derby first began, the Top Hat was worn. You rarely see that today. However I expect with the steampunk look being so popular we may see some interesting ones this year. Also,women are wearing these dolled up as a MadHatter or with netting.
Panama, Boat Hats, Bowlers and Derbys are all included in the mix.
One more hat that has been donned at the derby is the Driver or Ivy cap.
Like many celebratory events, the Kentucky Derby has also been taken to extremes when it comes to fashion and hats. You are certain to see some jaw-dropping hats decked out in bizarre decor and matching frocks and duds. But unlike most places, at the Derby these outlandish exhibitions are embraced and celebrated. So let your creativity flow if you plan to attend the Derby or a Derby party. Enjoy your self-expression.
So as we anticipate the upcoming event, select your hat to suit your style and personality and budget and add your dress, bow tie, shirt, shoes, parasol, clutch and jewelry to place the focus on that incredible hat! Because after all…It’s All About The Hat!
I would love to see your hats! Please send me pictures, I will add to my pinterest board.
If you enjoyed this post, please share to FB, Instagram, Pinterest, and Twitter.
Happy Planning!
Upcoming in the Series will include Menu, Bar Set Up, Wagers, Lawn Games and Contests and the event itself! Hope to have you join me again.
This Post is part of The Party Bloggers Link Party. To see other Posts in the Party Please use the Link below to go to our Host’s Site. I also linked up to Home Stories A-Z
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Such gorgeous hats! I find when we celebrate Melbourne Cup Day in November we tend to go for fascinators, but after reading your post I think a hat would be a nice change this year…
Fiona, I am so glad we have connected. I know little about Australia, except that my son-in-law’s family is from there. I have never heard of Melbourne Cup Day…perhaps you could share about it in November on your blog!
Thanks Debbie, I would love to do a post on Melbourne Cup Day. It will be spring for us then!
what time of year is it now?
This is a great article!! I secretly love hats, but have absolutely nowhere to wear them (and I have a giant head that is not conducive to women’s hat sizes). I just told my hubby that if we ever get to go to our real estate mentor’s annual Kentucky Derby party in Orlando, Florida, I now know what to wear. I would have gone to this party and concentrated on getting a great dress and been all wrong. It would be a hoot to get awesome hats for the hubby and myself!!
Thank you Melony….I’m a Realtor as well! Have never gone to a convention. Just started a couple of years ago to get into it for our retirement. My board is 4 hours away where our vacation rentals are so I am not real active yet. Mostly just family and friends of family for now. Hoping that my husband will want to get his license after her retires from Dentistry.
Super cute! I wish I was bold enough to rock some of these hats. I do have a secret desire to attend the Derby someday and look oh-so-fab while doing so. I’ll have to remember this post when that day comes! 🙂
Or throw one yourself! I will openly admit I am a bit terrified. I’ve never been to it but I want to throw the party. I believe I am a southerner at heart and love their traditions, fashion, food and accent!
This is so cool! So many hats, so many possibilities… I hardly ever wear a hat, but would make an exception for the Derby!
I have to confess that the first time you wear a hat in public it can be a bit intimidating because you will definitely get looks, but once you start having people tell you they secretly wish they could wear a hat and how much they love yours..well, you kind of realize you are giving them inspiration and perhaps they may get the courage to do something so crazy and fun. Thank you Marjan for reading and commenting, hope to have you back again!
Debbie, you make me want to wear a hat!! I love the idea!!
And you would look Marvelous Darling! 🙂