What to Wear


One of the truly unique characteristics of the Kentucky Derby, and its sister event, the Kentucky Oaks, is that they are sports parties that showcase the finest in spring fashions. Both female and male attendees pull out all of the stops when selecting their Kentucky Derby and Oaks apparel.

There are no hard and fast rules when it comes to Derby dressing, in part because what you wear has much to do with where you plan to spend the day. In the reserved seating areas (grandstand, clubhouse, suites and corporate hospitality areas), ladies typically wear spring dresses, pastel-colored suits, or bold separates that coordinate with their Derby headwear and accessories.

The Kentucky Derby is a chance for every female to express her inner Southern Belle so take note and don't hold back when planning your Kentucky Derby wardrobe!


When selecting your dress for the Kentucky Derby the recommended practice is to keep it simple, so it doesn't take away from your hat. You can also let the color and excitement of spring inspire you and select a dress full of color, or floral or equine patterns. Vineyard Vines, the official style of the Kentucky Derby, has created a line of dresses just for the Kentucky Derby. And remember to dress in layers, the Kentucky Derby is an outdoor event and the weather can be hard to predict.


No Kentucky Derby outfit is complete without the spring heel or sandal. But remember, Churchill Downs historic grounds can be tricky to maneuver and the day is long, so remember to pack a backup pair of flats, just in case!



Since the hat is the focus of Derby fashion, there's not much need for large, statement jewelry. Let your hat be the attention grabber as your primary accessory and keep the jewelry simple. You can also celebrate the day with Kentucky Derby themed jewelry.


The Kentucky Derby is a long day, with a lot of walking, so pack accessories accordingly. We recommend a large bag (but be sure to stay within the size limit) to carry a pair of shoes, a bottle of water, your program, sunglasses, sunscreen, a poncho, and anything else you might need during the day. In that bag, pack a smaller clutch or over-the-shoulder bag for your cash, wagers, phone, and essentials that you can grab to go make a wager or snap a quick picture of the celebrities on the Red Carpet.


What sets the Kentucky Derby and Kentucky Oaks apart from other sports and entertainment events? Is it the world-class horses? The Hollywood stars? The romantic Twin Spires? Well, first and foremost, it’s the hats! Part Southern tradition, part spectacle, the Kentucky Derby hat parade is much of what makes “The Greatest Two Minutes in Sports” one of the greatest people-watching events in the world! From the fantastic to the sublime, there are no rules or limits when it comes to choosing your Derby hat.

Wearing a hat to the Kentucky Derby is believed to bear good luck! The long-established fashion was started by the women, however, over the last few years, many men have taken part in the tradition as well. Wearing a hat is much like getting into costume, you might be pleasantly surprised to see what type of character you become. From the fantastic to the sublime, there are no rules or limits.

Within the seated sections of Churchill Downs, you will find hats of elegance and style. Generally speaking, women wear wide-brimmed, “Southern Belle” inspired Kentucky Derby hats. The hats can be decorated with flowers, feathers, bows and ribbons of any color to express creativity and individuality.

In the Churchill Downs Infield, hats are a bit more eccentric! You will see hats in all shapes and sizes, as well as some hats exuding humorous themes!

Jenny Pfanenstiel- A Featured Milliner

"A hat can not only change your day, but it can also change your life!" - Jenny Pfanenstiel

Jenny is a world-renown Milliner awarded and recognized for her skill of creating and sculpting hats by hand using the highest quality and rare materials from across the globe. The art of Millinery is a technique that dates back centuries through molding straw and felt over wooden hat forms which she takes great pride in applying with each one-of-a-kind hat, in addition to her unique process of sculpting hats on a braid machine from the 1800s. “The tradition of hats at the Kentucky Derby is just one of the distinctive things that make it such a sensational event and it is an honor to collaborate on one-of-a-kind head pieces that add to the beauty and special memories associated with America's Greatest Race.”

Jenny has crafted hats for some of the world's most well-known dignitaries and celebrities including Former First Lady Michelle Obama, Oprah Winfrey, Madonna, Neil Diamond, and Barbara Corcoran from the TV show "Shark Tank", to name a few. She has created exclusive hat collections for vineyard vines, J Peterman, Woodford Reserve, Goodman Theatre, Covet Fashion Style App, and the Joffrey Ballet and is a hat designer for McCall Patterns. In November 2015, Dover Publications published her methods in the book "The Making of a Milliner" to share her creativity with other aspiring Milliners. In 2019, she was selected as a Tory Burch Fellow through the Tory Burch Foundation as a woman entrepreneur.

Jenny is truly passionate about her craft and empowering those who wear her hats to feel confident and beautiful and looks forward to working with you to create that one of a kind piece.

Learn more about Jenny Pfanenstiel and view additional designs at A donation of 12% of purchase will be made to the Churchill Downs Charity Foundation when website offer is mentioned.

Christine A. Moore-A Featured Milliner

Christine Moore started her career in the world of theater as a costume designer and quickly began making hats for regional theatre productions. In 1990 she moved to NYC to work for renowned milliner Rodney Gordon where she spent four years making hats for Opera and Broadway productions such as Phantom of the Opera and Cats. In 1994 she established Christine A. Moore Millinery based in New York City on 34th Street between the fashion and accessories districts. Although Christine designs a wide range of women and men’s hats, she is best known for her explosive racing styles for the Kentucky Derby, four of which have been displayed in the Kentucky Derby Museum.

In 2020 she appeared as a contestant on the ABC game show To Tell the Truth where she stumped the celebrity panel. In 2019 Christine was featured in the Visit the USA; Kentucky Derby tourism film (part of the United Stories series) and was featured in the 2018 Netflix film 7 Days Out, a behind the scenes look at the Kentucky Derby.  In 2009 she partnered with Churchill Downs and Mattel to design the Official Barbie Derby hat, and in that same year her hats were featured on the official Kentucky Derby poster. Christine has been on Fox and Friends six times and the TODAY show eight times live from Churchill Downs where NBC calls her “The Milliner to the Triple Crown”. She has been named Featured Milliner of The Kentucky Derby six times and was the first milliner bestowed this title in Kentucky Derby history.

In 2022 she was commissioned a Kentucky Colonel - established in 1793 it is the highest title of honor bestowed by the Governor of Kentucky and recognizes an individual’s noteworthy accomplishments and outstanding service to the state of Kentucky and the nation. Christine is the official milliner for Breeders’ Cup, America’s Best Racing, the Iroquois Steeplechase, the Jim McKay Maryland Million Day, Thoroughbred Owners and Breeders Association (TOBA), and featured designer at the Preakness Stakes, Keeneland, and the Florida Derby.

Christine’s hats have graced many magazine covers including InStyle with Katy Perry, Vanity Fair with Jennifer Lopez, Sophisticated LivingSENSE Magazine, the Baltimore Sun, and was the first milliner to be showcased on the cover of Churchill Downs Magazine. She has designed for Jewel, Kirsten Collins, Kate Upton, Steffi Graf, Tara Lipinsky, Al Roker, Deborah Roberts, Dylan Dreyer, Tori Kelly, various Miss Kentucky and Miss Connecticut USA winners and many others. Her hats have been showcased on television shows including Nashville, The Carrie DiariesGossip Girl, and Horse Players.  She currently hosts The Christine and Kirby Show, a weekly Instagram show with Kirby Adams, a feature reporter and news anchor for broadcast television.

Christine A. Moore Millinery is known for their fine finishing work, attention to detail and customer service. Her designs are light in weight creating a softer and more wearable product. Each hat is individually made with great care in NYC, USA. Check out some of her designs below for inspiration or view her full line at at Use promo code KYDERBYFEATURED149 for 15% off your purchase

Featured Milliner Christine A. Moore Advice/Hat Tips:

  1. Most important! - Hats are all about personality, especially for the Kentucky Derby! If the style fits your personality, start there and then let us help you customize the hat to fit everything else about you! It is important to consider brim size, crown size and your head measurement. We always want the proportions to be spot-on and fit you comfortably for the entire day!
  2. Hat or Dress first? We say either! Find the hat or dress that speaks to you and the rest will follow. We are always here to help either way!
  3. Match or not to match? Matching is certainly eye-catching and sometimes elegant, but blending is always elegant. Again, it goes back to how you want your audience to view you and your personality.
  4. The Kentucky Derby is actually a 2 day fashion event. Oaks on Friday and the Derby on Saturday. Do I have to wear specific colors to either one? Not at all. The Kentucky Derby is a chance for guests to express themselves through fashion, and you will see every shade and hue and lots more represented! Many women and men will incorporate various shades of pink into their outfits on Oaks day and some will incorporate floral shades of red into their looks on Derby Day in support of the nickname “Run for the Roses”.
  5. Do men really wear hats to the Derby? Yes! A sleek fedora trimmed in colors to match a suit is timeless and always a classic look. Choose straw over felt and you will be cooler!

The bottom line is you want to be comfortable, look great, have the best time ever and all the photographers will find you! Happy Derby!

To learn more about Christine and her Collections go to:

The Hat Girls

Born and raised in Louisville, Kate and Rachel have been best friends for over 20 years since attending high school together at duPont Manual. Upon graduating, they left Kentucky to explore their creativity in the world of fashion and beyond.

In 2013, from New York City & Las Vegas, they returned to Louisville for the Kentucky Derby as The Hat Girls, intent on creating wearable art for women from all walks of life. Utilizing their natural eye for design, the girls create everything from the classic "Southern Belle" style Derby hat to extravagant, show-stopping headpieces.

Kate Smith completed her study of fashion design at Columbia College in Chicago. Rachel Bell loves to create and is the consummate “people” person, with a flair for marketing The Hat Girls creations.

Whether you desire a funky fascinator or a couture millinery piece, The Hat Girls have you covered for the Kentucky Derby and all other special occasions!

Learn more about The Hat Girls and view more of their designs at

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The Kentucky Derby provides a splendid excuse for men to get just as dressed up and decked out as the ladies! The modern Derby man possesses an unparalleled color palette. Sun-drenched, tropical colors in bold stripes or busy plaid and bright pastels steal the limelight. Although, if you want a more polished look, a classic navy or seersucker blazer is always in style.

Starting with the pants because it is the eye-catcher from a distance, gents should turn to sun drenched pants in vibrant colors like Key Lime, Ocean, Bermuda Pink, and Citron. Any one of these colors paired with the right shirt and blazer will make you stand out like no one else.

Now that you have the pants you know that you’re going to have some fun with the shirts. A great dress shirt in a complimentary color will go a long way. Don’t be afraid to grab a fun gingham or striped shirt to turn it up. This is the one day of the year that more is better. One option that is a must for some is the monogram on the shirt!

The jacket is what brings everything together and you can’t go wrong with the classic navy blazer. If you want to have a little fun on top though, a nice chalk stripe can really make the ladies’ big hats turn. As far as 2- button or 3-button it’s a person preference but we recommend sporting the 3- button side vent for a more polished look.

Next is the tie. Most gentlemen wear a necktie, but a bow tie is always a great option. If you never wear bows, try it out and you may like it. As the official style for the Kentucky Derby, vineyardvines offers an assortment of Derby-themed ties and bowties that will make every man look dapper and distinguished.

For shoes, there are many types of horse bit loafers out there and everyone has their idea of who makes the best ones. The most important thing you need to know is that they should be worn sockless.

Top it all off with a fedora or bowler hat for the complete Kentucky Derby look. Men's Derby hats are generally solid in color and inspired by the style from the 1920s.

Now you are ready to throw back some bourbon and tie on a bowtie. The most important thing about your Derby outfit for men is to be confident. No matter what you wear, it’s how you wear it gentlemen.