2021 Kentucky Derby: Run for the Roses fashion trends and hats


Hats are as popular as the horses at Churchill Downs during Kentucky Derby weekend. But one might affirm there’s a new fashionable accessory taking the stage at the 147th Kentucky Derby on May 1. 

Face masks are the new must-have, and not just because of Kentucky’s executive order that requires the use of face coverings in most public settings. Let’s find out some of the fashion trends ahead of the big races this weekend.

Will masks be part of this year’s Kentucky Derby fashion?

Starting in 2020, milliners have added face masks to their collections to properly match the hats they create.

While some designers have opted to create fancy masks, others like Rachel Bell and Kate Smith thought to keep the face covering accessory neutral and of one shape.

“It’s all about the hat, we want the attention to be on the women’s headwear and on their dresses,” Bell said. “The mask should really blend with the outfit, because the focus is on the hat.”

Bell and Smith, owners of The Hat Girls, are the official hat designers of the Kentucky Derby Festival for the sixth year in a row. While they created 720 hats for this year's race, they are also offering 32 different shades of colors they can pull from the dresses or hats to create the perfect matching face mask, outsourced from Peake Ties.

And when it comes to masks, as it is with hats, there’s no limit to transforming a simple idea into a glamorous artcraft. They come in any color and material, and some milliners decorated them with applied flowers and butterflies, as well as feathers and rhinestones.

Where does Kentucky Derby fashion originate from?

Hats have been a Kentucky Derby tradition since its debut in 1875, when Colonel Meriwether Clark Jr. decided to model the race after British horseracing, with strict dress codes for women and men -- which, of course, included the unique accessory.

According to Jessica Whitehead, curator of collections at the Kentucky Derby Museum, the Derby owes most of its fashion traditions to its European predecessors.

“Beautiful, cutting edge fashion was a main staple of European racing, and the Derby fashion tradition, like many of its traditions and rules, was greatly inspired by the European systems,” Whitehead said. “Dress codes are still in effect for the grandstands of many European tracks.” 

Clark, who founded Churchill Downs, traveled to France and England with his wife Mary, noticing how well-dressed pageantry was at horse races. They brought the style and fashion back to Louisville, with Mary encouraging women to dress up and show their best outfits at the Kentucky Derby.

These fashionable outfits included, of course, hats. According to Whitehead, the accessory began a tradition of the Derby “very organically.” Since hats were an essential part of women and men’s closets, they were a distinguished element at the racetrack too. 

After World War II, hats started being worn for special occasions like the Derby, as they no longer had a special place in women's and men’s wardrobes. 

“As hats began to go out of fashion in everyday wear, somewhere around the late 1960s and early 1970s, Derby became one of those few special occasions in the United States where hat wearing was a special treat. Finding a Derby Hat became a fun ritual.”

When the race was first televised in 1952 -- coincidentally or not -- the audacious hats we know today started to emerge, with women wearing extravagant larger, wilder and wackier headpieces to stand out from the crowd and garner attention. 

Afterall, as Whitehead said, “a major draw at the Derby is being seen by other people who are there.”

Hats are now a symbol of the Run for the Roses. It doesn’t matter if you decide to wear a wide-band hat, a sunhat or a fascinator (which is a headpiece attached to a clip or headband). The Derby is like a runway where people want to be seen and be part of its experience.

“The Derby is a feast for the senses, just like the smell of roses, or the taste of mint, or the sound of the Call to Post,” Whitehead added. “The hats have become a colorful reminder of the huge, diverse range of people who love the Derby for all different reasons.”

What are popular Kentucky Derby hats this year?

Women usually wear wide-brimmed “Southern Belle'' inspired Kentucky Derby hats, which can be decorated with flowers, bows, ribbons or feathers and can come in any color. Expect to see a lot of men wearing fedora hats too, with the common rule to match them with their outfit. 

But as fascinators are getting more and more popular over the years -- thanks to fashion icons like Meghan Markle and Kate Middleton, Rachel Bell of The Hat Girls thinks they will take the stage this year at Churchill Downs because of the mandatory use of face masks.

“We found it easier to convince people to go with a fascinator because it’s not covering your face as a big hat would do,” Bell said. “With a wide brim all you are going to see is the eyes, if you have the mask and sunglasses on.”

Fascinators and hatinators are also easier to wear with face masks. Because these hats sit on a headband, you can take your face covering on and off quickly whenever you have to drink or eat. 

The big brims are still a tradition of the Kentucky Derby. Expect to see a lot of them worn in any color on May 1, from indigo to bright yellow, but also orange, greens and various shades of purples, matched with face masks of the same color.

What are the trending outfits for the 147th Kentucky Derby?

The Kentucky Derby can be a very hot day, and standing for more than 10 hours watching horse racing convey only one rule: wearing comfy, but stylish, outfits. 

The key to surviving a hot Louisville day is the material. Avoid polyester and opt for cotton, silk or linen. Vegan leather in various colors is one of the trending materials this year, especially for jackets and skirts. 

Heels and spring sandals are a fashion must for the ladies, while horse bit loafers or anything sockless are the perfect shoes for men to wear at the race.

Some of the 147th Kentucky Derby trending outfits for ladies are not just dresses and skirts.  Pants (especially joggers), jumpsuits and rompers have become staples in women’s closets after a year of at-home outfits, and will be shown off at Derby week. 

Despite the latest trends, Bell does think the event will spark people’s passion towards fashion.

“I think people will tend to dress up a little more this year,” Bell said. “Since we have been at home wearing athleisure for the last year or so, we expect to see really nice outfits out on the tracks.”

A men’s must-have this year is anything floral -- you read it right. Flowers this year are not just for women, with jackets, suits, pants and shirts blooming in floral prints. For those who are not a floral lover, they can always opt for eye-catching pants in colors like indigo, ocean, greens and purple.

Something pink, a decade-old color tradition at the Derby and considered by most the “official color” of Oaks Day, is another must-have to wear at Churchill Downs. 

“Pink is a huge color,” Bell said. “Men and women typically just pull it into their outfit, whether it’s for Friday or Saturday.”

Many couples will opt to coordinate their style in an elegant way, whether it’s with an accessory -- like a necktie for him that blends with both her dress and hat color -- or tying the outfits with coordinating masks. 

Finally, always be prepared in case of rain. The forecast for May 1 says rain is unlikely, but a clear rain jacket or poncho is what everyone needs to make their Kentucky Derby outfits still visible on a rainy day. One can always be fashionable with a pair of extravagant rain boots, but remember: umbrellas are not allowed inside Churchill Downs.

And you’re off!

Watch the 147th running of the Kentucky Derby on Saturday, May 1 from 12:30 to 2:30 p.m. ET on NBCSN and from 2:30 to 7:30 p.m. ET on NBC. Full coverage is also available on NBCSports.com and the NBC Sports app.

Written by Gaia De Simoni 

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