The 10 Craziest Kentucky Derby Outfits Of All Time

On the first Saturday in May, many from far and near find themselves making their way to the South for a yearly tradition that has taken place in America for centuries. The annual Kentucky Derby, which has run consecutively every year since 1875, has drawn the attention of many elite members from high society, including Queen Elizabeth II. The event is more than just an excuse for guests to sip on the traditional mint julep drink, it is known as "The Most Exciting Two Minutes In Sports", because of the thrill of watching various horses duke it out for the coveted Triple Crown.

While the race, that is held in Louisville, Kentucky, is a competition for thoroughbreds, the event is also known for its outlandish display of outfits worn by its attendees.

From large hats to bright suits, the fashion at the Kentucky Derby is highly-anticipated, and the guests, particularly the celebrities, never disappoint. Here are the 10 craziest outfits worn at the Kentucky Derby.

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10 Gren Wells

This Kentucky-born actress and filmmaker, made quite an appearance at the 2016 Kentucky Derby when she wore an unusual, intricate web-like headpiece, but was very proud of it.

Gren Wells, who is best known for writing the script for the romantic-comedy A Little Bit of Heaven, was accompanied by film producer, Brent Emery, and complimented the headpiece with a simple low-cut white and black dress.

9 Joey Fatone

Since his days singing hit songs, such as "Bye Bye Bye", Joey Fatone has always been known to steal the spotlight, so it's no surprise that he did the same at the 2019 Kentucky Derby. The former NSYNC member, who is also known for his media and television appearances, was the talk of the town with his all-blue ensemble.

While he opted to wear a more laid-back hat, this still may not be a traditional outfit one would wear in any other occasion.

8 Kate Upton

The wildly, beautiful model-actress Kate Upton, joined in on the popular trend of wearing large, over-the-top hats. While the hat she wore in 2016 wasn't too distracting, it still made a statement.

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Upton, who is best known for her roles in the films, The Other Woman, The Layover, and The Disaster Artist, wore a classy-fitted green dress, silver pumps, and a winning smile to go with the white hat.

7 Star Jones

Star Jones is a star, there's no doubt about it. From her time on the popular daytime talk show, The View, her style has spoken for itself, most notably the 27 foot train she had on her wedding dress.

At the most recent Kentucky Derby, however, Jones' was slightly upstaged by another star, her dog. The former lawyer and journalist arrived at the red carpet with her adorable dog who wore a black and white dress that matched her's. To top it off, Jones' wore a feathery-black hat to add to the flair of her outfit.

6 Dannielynn Birkhead

The world watched Dannielynn Birkhead grow up and she has been making her mark in the entertainment industry. Birkhead is the daughter of the late model-actress, Anna-Nicole Smith, and Kentucky-native, Larry Birkhead. After the tragic passing of her mother, Dannielynn was unwittingly thrown into a the spotlight due to the paternity case between Birkhead and several others. After it was announced that Birkhead was Dannielynn's biological father, the two have been inseperable.

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The father-daughter duo have been attending the Kentucky Derby since 2010 but there most memorable outfit was in 2013 when they dressed as Mary Poppins and Bert.

5 Nene Leakes

The Real Housewives of Atlanta star, Nene Leakes, is known for her no-nonsense attitude and unapologetic personality. It's only fitting that her outfit for the 2019 Kentucky Derby has a personality of it's own as well.

The beautiful mom of two arrived at the festivities with a yellow ensemble with a headpiece that had pink, orange, and yellow flowers on it. In addition to the flowers, Leakes had butterflies attached to it adding to a playful look.

4 Jessica Simpson

In 2004, singer and actress Jessica Simpson attended the Kentucky Derby with her then-husband, Nick Lachey. While Lachey chose to wear a classy suit and tie, Simpson made a statement with her larger-than-life pink hat to go with her floral pink dress.

The couple would later go on to divorce and marry again, but they will always be remembered for time on their reality-television show, Newlyweds: Nick and Jessica, and their fashion choices.

3 Mira Sorvino

Actress Mira Sorvino, best known for her roles in Romy and Michele's High School Reunion, Summer of Sam, Mimic, and Mighty Aphrodite, stole the show in 2017 when she arrived at the Kentucky Derby.

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Sorvino also sported a large hat that may have covered her hat but complimented her black, pink, and white dress. The hat also had a pink on top, giving a subtle nod to southern-style. Her husband, actor Christopher Backus, matched her with a simple, pink and white suit and black tie.

2 Chef Johnny Iuzzini & Gia San Angelo

Chef Johnny Iuzzini arrived at the 2018 with Gia San Angelo wearing a platinum tuxedo-jacket and grey hat, while his date wore an unusual hat that matched her simple pink dress.

The chef's appearance caused a bit of a controversy, due to the allegations of sexual misconduct Iuzzini is currently facing that also led to his termination from the baking show, The Great American Baking Show.  Despite this, the couple were all smiles and also join the ranks of wearing one of the most memorable outfits.

1 Priscilla Barnstable and Patricia Barnstable-Brown

Identical-twin sisters, Priscilla Barnstable and Patricia Barnstable-Brown, are Kentucky royalty and their outfits are proof of that. The actresses and daughters of the former NBA Dale Barnstable, have worn many memorable and bizarre outfits to the Kentucky Derby but their 2015 large-matching silver hats with white and grey flowers is probably the most unforgettable.

The twin actresses best known for their roles in the show, Quark, are also heavily involved in finding a cure for Diabetes, having raised $2 million with their sister and mom through their foundation, Barnstable Brown Foundation.

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