
How to pick a Kentucky Derby hat for women
Looking for a Kentucky Derby hat? Here the three pro tips to help you pick the best hat for your Kentucky Derby outfit.
It is time to start thinking about what you will wear for the 2025 Kentucky Derby, held this year on Saturday, May 3.
Whether you’re in the infield or the grandstand, you want to dress to impress. Need some inspiration? Here are nine fashion shows you can attend to see what are the top fashion trends are for spring and the 2025 Kentucky Derby.
2025 Kentucky Derby fashion shows
WHAT: Enjoy cocktails and hors d’oeuvres as you bid on over 250 Kentucky Derby hats and fascinators and other items. Proceeds benefit Kosair for Kids Child Abuse Prevention Fund.
WHERE: The Olmsted, 3701 Frankfort Ave.
WHEN: March 13, 5:30 p.m.
COST: $40
MORE INFORMATION: kosair.org/events/hats-on-for-healing.
WHAT: This Kentucky Derby themed fashion show is named in honor of a former Brown Cancer Center patient, Kim Heath, and features patients and providers from Brown Cancer Center modeling hats, brunch and shopping opportunities. Proceeds to benefit University of Louisville Health – Brown Cancer Center.
WHERE: Mellwood Art Center, 1860 Mellwood Ave.
WHEN: March 16, 11:30 a.m. to 2 p.m.
COST: $100 single, $800 for a reserved table of eight
MORE INFORMATION: one.bidpal.net/HatsforHope25/welcome.
WHAT: Show off your most glamorous hats and mix and mingle with fellow Kentucky Derby hat enthusiasts. How it works: bring a gently used or new Kentucky Derby hat to participate and find a new hat from a huge selection. Find a hat you love, exchange your hat for a new one as many times as you want over the course of the event. There will also be a silent auction with Kentucky Derby Hats, liquor, spirits, apparel, home decor, experiences, jewelry, and fun Derby-related items and a pop-up boutique to round out your fit. Items will be auctioned online — you can bid even if you’re not attending the event. Don’t have a Kentucky Derby hat? There will be extras for sale.
WHERE: Biscuit Lounge, 120 S. 10th St.
WHEN: March 22, 11 a.m. to 2 p.m.
COST: $50
MORE INFORMATION: Proceeds benefit Dress for Success Louisville programs. louisville.dressforsuccess.org/get-involved/events.
WHAT: Kick off the Kentucky Derby season in style. See the latest couture designs for women and men from the Kentucky Derby Museum’s featured milliners at this one-of-a-kind event. Enjoy complimentary mimosas, bloody marys, premium gin cocktails and shopping opportunities. Grab some brunch bites before the models hit the runway to show off the latest hat and jewelry trends. DJ will keep the party going while milliners help you plan your signature Kentucky Derby look.
WHERE: Kentucky Derby Museum, 704 Central Ave.
WHEN: March 23, 10 a.m. to 1:30 p.m.
COST: $75, $40 for ages 18 and younger; $125 for VIP, includes front row seating and swag bag.
MORE INFORMATION: derbymuseum.org/hats
WHAT: See the latest spring fashion trends and accessories for the Kentucky Derby season from Dillard’s and local boutiques as they come down the runway at this annual style extravaganza including fascinators and chapeaus. It’s the place to find your Kentucky Derby Festival must-haves along with what to wear for the upcoming season. For ages 21 and older.
WHEN: March 27. Boutique shopping and cocktails at 5 p.m., followed by dinner at 7 p.m. and the fashion show at 8 p.m.
WHERE: Caesars Southern Indiana, 11999 Casino Center Drive, Elizabeth, Indiana
COST: $150 per person or $1,500 for a table of 10 for showroom/main floor seating and includes reserved dinner seating, wine, event pin, swag bag and show.
MORE INFORMATION: kdf.org.
WHAT: An exclusive evening with milliner Jenny Pfanenstiel. Choose between a fascinator, fedora, or brimmed hat to create your very own one-of-a-kind hat with expert guidance to show off at your upcoming Kentucky Derby events.
WHERE: Whiskey Thief Distilling Company, 610 Nanny Goat Strut
WHEN: April 9, 5:30-8:30 p.m.
COST: $125 for fascinator; $285 for fedora
MORE INFORMATION: brushfire.com/whiskeythief/pfanenstiel2025/597575/details.
WHAT: Waterfront Botanical Gardens is hosting its fourth annual fashion show and luncheon featuring Kentucky Derby-season accessories for both men and women. Explore vendor pop-up shops after the event.
WHERE: Waterfront Botanical Gardens, 1435 Frankfort Ave.
WHEN: April 10, 11:30 a.m. to 1 p.m.
COST: $100
MORE INFORMATION: Proceeds to benefit Waterfront Botanical Gardens programs. waterfrontgardens.org/fascinator.
WHAT: The runway-style show presented by Dillard’s includes models showcasing men, women and children springtime apparel. Models represent more than 18 parishes in the Louisville area plus scholarship students, and Miss Kentucky, Chapel Tinius. Shannon Cogan from WAVE News is the host.
WHERE: Crown Plaza Hotel, 830 Phillips Lane
WHEN: April 10. Doors, 11 a.m.; lunch/show, noon
COST: $65, $800 patron table for 10
MORE INFORMATION: queensdaughtersinc.com/upcoming-events/2025-fashion-show-and-luncheon.
WHAT: The 15th annual fashion show features a day full of Kentucky Derby fun with a fashion show, food, networking, sipping, silent auction, surprises, and more. Shopping, 9 a.m.; fashion show, 11:30 a.m.
WHERE: Grand Ballroom, Louisville Marriott East, 1903 Embassy Square Boulevard
WHEN: April 10, 9 a.m. to 2 p.m.
COST: $100 single (not reserved), $1,000 for a table of 10 reserved seating through April 1; $125 single (not reserved) and $1250 for a table of 10 reserved seating after April 1.
MORE INFORMATION: eventbrite.com.
Reach Features News Clerk Gege Reed at [email protected].