Iconic Kentucky Derby Hats That Should Never Be Forgotten

The Kentucky Derby is coming up in May and if you’re a fashionista, this event means more to you than a horse race. The Kentucky Derby is known for capturing the most iconic hats on the world’s most iconic women. This is one of the oldest fashion traditions and we can’t wait to see the hats this 2020! But, we have to look back on the styles that should never be forgotten!

Krysten Ritter

Back in 2013, Krysten wore a very classy and elegant hat. This has to be one of my favorites! This oversized hat is a cream color that has blue accents around the brim and a blue bow that wraps around the body of the hat. She paired it with an elegant floral dress that looks so Beautiful!

The Queen

The Queen is known for her colorful and quirky style. Not only has she been spotted matching colors back home, but she has been spotted at the Kentucky Derby matching her outfit with her hat! We are living for it! Back in 1991, The Queen attended the derby wearing a bright green oversized hat with a bright pink bow attached! The pink and green make a bold statement, not to mention she is matching her green hat to the rest of her look!

Jessica Simpson

Jessica Simpson is one of the world’s most shocking dressers, dating back to her denim on denim look. At the 2004 Kentucky Derby race, Simpson was spotted wearing a gigantic candy pink hat. The hat looked as if it was a beachy style! This is one of my favorite looks from the Kentucky Derby. Jessica Simpson looks absolutely stunning. She paired this hat with a colorful dress that throws us back to 2004, but don’t you just love it! She remains such an icon!

Kim Kardashian

Who other than Kim Kardashian to make an appearance at an event like The Kentucky Derby! Back in 2009, she gave off an old Hollywood vibe with a dark grey hat with feathers coming out of the side. Along with the hat, Kim wore oversized shades and a bright white dress!

Kate Gosselin

Kate was seen in 2011 sporting an oversized black hat that had a bunch of feathers draping over the brim. As well, the top of her hat had the material of a tutu coming out! It was so over the top that we had to count it as one of the most iconic hats to date!

Sarah Hyland

Not that long ago, in 2015, Sarah Hyland was seen rocking the opposite of oversized. She wore a small red floral accessory in her hair that contained two long feathers coming out the back, along with a red netting covering a part of her face.

Johnny Weir

Again, in 2015 Johnny Weir’s hat included a mohawk of red roses. Not only was this bold and extravagant, but inside the roses a cocktail was hiding! It was a cool twist on the Derby hat because there was function behind the style too! This is one of the most iconic hats that we have seen to date!

Cassandra Jean

This actress strayed away from the trend of pastels in 2016 and went down her own color path. She sported a dark purple oversized hat that had flowers going along the body of the hat with fabric coming out everywhere! This hat was drop dead gorgeous!

Rachel McCord

McCord went off the beaten path in 2016 as well and wore what looks to be a hat flipped upside down. This hat features a cream color on the outside, with a baby pink lining the inside and the brim. In the middle of the hat there is an arrangement of pearls. So elegant!

Kate Upton

The beautiful Kate Upton proved to us the point that less is more. She sported a plain white oversized hat. She paired this with a dark green dress. This look is so iconic and proves that you do not need to go all out to look absolutely stunning at the Kentucky Derby!

Giada De Laurentiis

Giada looked absolutely stunning in 2016, how could we forget! She wore a bright yellow hat that was very oversized and included a silk yellow ribbon tied around it and a big yellow flower coming out of the side. This is one of my favorite looks from the Kentucky Derby. Pastels have always been the go to for Derby goers and it is such an elegant look! Giada definitely goes down as one of the most iconic looks from the Derby!

Victoria Justice

In recent years, 2018, Victoria Justice looked gorgeous sporting a jet black hat with a feather going from front to back. She paired this with an all white suit which made the hat pop! She also used a black studded handbag that matched perfectly to the hat. This is hands down one of the best looks the Derby has ever seen!

Coco Rocha

In 2013, wore a simple yet elegant styled hat. The hat was very well designed and looked extremely intricate on her head. There were flowers flowing out of the hat and they were bright purple. The purple color paired perfectly with her light purple suit.

Brooke Shields

Brooke wore an electric blue colored hat that was simple until the brim. Surrounding the brim, there was netting that went down and covered her entire face! The top of her hat was simple and encompassed a ruching design. She paired this with a simple and elegant white dress.

Tara Lipinski

Former figure skater, was seen in 2014 looking like a hot pink cupcake. She wore a flowy hot pink dress. The dress matched the hat and was oversized with a big pink flower coming out of it. This is one of the boldest and brightest looks to hit the Derby red carpet since 2014!