Hats, Heels & Southern Charm: Kentucky Derby Outfits for Women Who Love To Make an Entrance
Embrace Derby Day with these fashionable looks!
The Kentucky Derby will take place on May 3, 2025 at the historic Churchill Downs in Louisville, Kentucky. Millions of viewers will tune in to watch the “most exciting two minutes in sports” and most of them will be dressed to the nines for the occasion. Whether you’re attending the derby in person or hosting a Derby Day gathering to watch on television, dressing up is part of the fun! Here are 30 ideas for classy Kentucky Derby outfits women over 50 can feel confident in.
Bright Colors for the Kentucky Derby
Ruffles, bright colors, and sparkling blazers are the name of the game for some when it comes to feel-good fashion. If those elements are what you’re drawn to, you’ll love this clothing for the Derby! Don’t forget to check out deals on Derby clothes at Amazon, too!
- Anthropologie The Colette Cropped Wide-Leg Pants by Maeve: Linen Edition, $138
- Free People Lizzie Sweater Top, $48
- Johnny Was Delaney Short, $59 (orig. $198)
- Johnny Was Joanna Blazer, $85 (orig. $280)
- Zadig&Voltaire Satin Rayon Dress Green, $448
Pastels for the Kentucky Derby
If pastel hues are more your style, we’ve got the perfect styles for the Kentucky Derby! From Free People printed sets to mini dresses from Good American, shop these pastel styles to find your perfect Derby wear.
- Free People Gesibelle Printed Set – $168
- Good American Satin Mini Dress – $199
- Kut From the Kloth Katara Top – $69
Pieces with Volume for the Derby
If you love clothing that goes the extra mile, you’ll love these pieces with a bit of personality. We’re talking flouncy sleeves, pronounced shoulders, and so much more.
- Ann Taylor Floral Square Neck Blouse – $54 (orig. $90)
- Johnny Was Linen Chevron Tank Dress – $280
- Kut From the Kloth Meg High Rise Wide Leg – $109
- Anthropologie Hanky Cropped Cutwork Tank – $108
Hats for the Kentucky Derby
For women, a hat is a must when it comes to Derby Day attire. A big hats is a “woman’s crowning glory” when it comes to getting dressed up, especially when it comes to the Kentucky Derby! These Derby-approved hats are some of our favorites.
- Free People Shady Character Packable Wide Brim Hat – $68
- DSW Kelly & Katie Pop Band Fedora – $30
- DSW Kelly & Katie Trimmed Floppy Hat – $35
- Ann Taylor Weekend Collection Tie Visor – $30 (orig. $50)
Women’s Shoes for the Kentucky Derby
No outfit is complete without the perfect pair of comfortable shoes. Stand tall all Derby Day long with these fashionable yet functional styles.
- Ann Taylor Flower Nip Toe Leather Slingback Flats – $94.80 (orig. $158)
- DSW Kelly & Katie Heather Sandal – $53.99
- DSW Florsheim Postino Cap Toe Oxford – $109.99
- Zadig&Voltaire Cara Ankle Boots – $698
Women’s Accessories for Derby Day
Complete your Kentucky Derby style with the perfect accessories. From purses to jewelry, sunglasses, gloves, and even an umbrella for potential rain (or to block the sun), we’ve got you covered when it comes to the best accessories.
- Case-Mate Special Edition Bow Beach Tote With Phone Pouch – $100
- Dana Rebecca Designs Diamond Huggie Earrings – $496
- Frank Darling Bezel Set Split Shank with Diamond Details -$1,640
- gorjana Horse Parker Charm – $38
- Lovisa Waterproof Gold Plated Stainless Steel Diamante Horseshoe Hoop Earring – $4 (orig. $18)
- Melinda Maria Isla Tennis Necklace – $235
- Brahmin Lane Purse in Songbird Melbourne – $265
Want to rent your Kentucky Derby clothes instead? Rent the Runway makes it simple to style yourself in designer looks. Plus if you really love what you wear, you can purchase the look at a discounted price
Hosting for Derby Day?
What would a Kentucky Derby party be without the right food, drink and decor? Find alcohol near you with Saucey or Minibar and have the bourbon of your choice delivered right to your door. And don’t forget these hosting essentials for your Derby party:
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Stags’ Leap Whites & Roses – $28+
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Book Outlet Browse Horse Coffee Table Books – Prices Vary
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19 Crimes Snoop Dogg Cali Rose Gold (Limited Release) – $18
Need even more shopping? Keep reading:
Macy’s Great Shoe Sale Is Here: Save Up to 40% on Heels, Sandals and More
Zappos Has Unique Mother’s Day Finds for the Mom in Your Life
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