Today Show: Best Kentucky Derby Hats & Kentucky Derby Fascinators


Today Show: Best Kentucky Derby Hats

I have to confess to you right now, I know absolutely nothing about the Kentucky Derby, horses or hats. So this segment was extremely weird for me. But on the Today Show May 2 2013, Al Roker did a segment searching for the “best” Kentucky derby hats. “Best” doesn’t mean “good-looking,” although you’d think that it would. “Best” apparently means most ridiculous. They asked viewers to send in pictures of their hats for the derby and the three finalists came in to show off their hats. And they all looked pretty silly. But if the Kentucky Derby is filled with a sea of goofy hats and these hats were the most ridiculous, I guess that’s something, right?

Today Show: Best Kentucky Derby Hats & Kentucky Derby Fascinators

Apparently at the Kentucky Derby, no one is watching the horses because everyone’s so fascinated with all the weird hats in the audience.


Celebrity Fashion Expert Weighs In On Derby Hats

Al Roker invited a celebrity fashion expert to come by to judge the hat contest. The expert said she is looking for “punctuation, creativity, uniqueness.” Okay, so now I know the criteria. We are looking for the most ridiculous and unique hat in all of Kentucky. Two of the ladies were from outside Kentucky (Utah and Tennessee, respectively) but you get the point. These are the ladies that will part crowds at the Kentucky Derby as people wonder, “What the heck is that on your head?” Since I’m really clueless on how to judge these hats, I’m just going to give out my own awards. And each lady will get one, so they’re all winners!

Paper Rose Kentucky Derby Hat

Brittany from Provo, Utah had a paper rose hat, which looked a bit like a gigantic pop-up book sprouting from her head. It was very unique. It had “expression” which the fashion expert thought was important. Brittany said she got the idea after making huge paper flowers for her bouquet and her centerpieces at her wedding. Later, she and her husband went to the royal wedding in England and she decided she needed a unique hat, so she made a gigantic paper rose hat.

Brittany said she thought everyone was going to be wearing huge hats at the royal wedding, but only the people in the church were, so she was kind of out of place. This is either the saddest story or the most awesome. She was walking around England on the day of the royal wedding, rocking a gigantic flower hat? I think that’s really cool.


Brittany also wins my “Most Nice” award because you could just tell from her demeanor and the way she interacted with the judges that she was just a really nice person.

Butterfly Kentucky Derby Hat

Connie came from Memphis, Tennessee and had a hat covered in fake flowers and butterflies. There were seven butterflies because Connie always hangs out with seven ladies who call themselves “The Magnificent Seven.” Two of them were breast cancer survivors, so she incorporated pink into her hat, and one of her friends had ovarian cancer, so she added blue to the hat. It’s really neat she incorporated personal elements into the hat, but I think her hat is my least favorite. But she should win the award for “Most Personal Hat.”

Fascinator Kentucky Derby Hat

Deana from Louisville, Kentucky should win the award for “Most Normal-Looking Hat.” There was some debate on whether her hat actually counted as a hat, since she used a headband fascinator to keep it on. Deana said she did this because there are a lot of events after the Kentucky Derby, and the fascinator/headband keeps her from getting hat hair. Her hat sat on her head at a jaunty angle. It was pink with a feather in it.

Because Deana was the only one actually from Kentucky, and because her hat was the most fashionable, I’m voting for her for “Best Hat.” But once again, what do I know about Kentucky Derby fashion? Let’s see which of these ladies won the award on Today.

Winner Of the Kentucky Derby Hat Competition

The winner is….drum roll, please…Brittany, the paper flower hat wearer! Not only did she win my “Most Nice” award, but she also got the trophy for Best Hat! “Best day of my life,” Brittany said.

Al Roker asked Brittany if she was married and Brittany said she was. Al Roker wondered if this moment was better than her wedding day. Brittany looked embarrassed and said she shouldn’t answer that question on TV, but it was definitely among her best days. Meanwhile, Deana and Connie stood around awkwardly in the background.

So, there you go, people! The way to judge a Kentucky Derby hat is by looking for the most unique and ridiculous hats out there. Brittany wins with flying colors.


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