Classy Kentucky Derby Outfits for Women Over 50
Embrace Derby Day with these fashionable looks!
The 2024 Kentucky Derby will take place on May 4 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.
Kentucky Derby Outfits for Women
- Bright Derby Top: Ann Taylor Ruffle Halter Top
- Anthropologie Dress for the Kentucky Derby: Significant Other Strapless Midi Dress
- Maxi Dress for the Kentucky Derby: Marina Joy Silk Maxi Dress
- Womens Gold Glitter Print Suit Jacket: The Gold Dust
- Crisp White Polo: Air Polo
- Pastel Ann Taylor Dress for the Derby: Short Sleeve Flare Dress
- Plaid Strappy Dress for the Kentucky Derby: The Savannah Swinger
- Comfortable Women’s Pants for the Derby: Sonora Stretch Terry Pant
- Pastel V-Neck for the Kentucky Derby: Women’s Chalk Pink V-Neck
- Floral Print Dress for the Derby: Daphne Silk Maxi Dress
- Women’s Button Down for the Kentucky Derby: Presley Crop Button Down Top
- Floral Top for Derby Day: Renata Floral Front Twist Button-Up Top
- Light Blue Caned Wicker Wrap Dress for the Kentucky Derby: The Porch Swing
- Puffy Sleeve Top for the Kentucky Derby : Mare Mare Puff-Sleeve Off-The-Shoulder Mini Dress
- Puffy Long Sleeve Derby Dress: Arianne Elmy Good Luck Dress
- Halter Dress for Derby Day: Pleated Halter Flare Dress
- Yellow Women’s Derby Hat: Sun Drench Felt Hat
- White Hat for the Kentucky Derby: Crown Vintage Felt Panama Hat
- Women’s Fedora for the Kentucky Derby: Kelly & Katie Chainlink Fedora
- Statement Sandals for Derby Day: Floral Statement Sandals
- Pastel Sandals for the Kentucky Derby: Vince Camuto Faiza Sandal
- Women’s Mules for Derby Day: Carina Cross Strap Mule
- Heeled Sandals for the Kentucky Derby: Journee Collection Melissa Sandal
- Purse for the Kentucky Derby: Carrie Convertible Clutch
- Bracelet for Derby Day: Carter Gemstone Bracelet
- Chunky Deco Inspired Bezel Set Pendant: The Radiator e.w. Emerald
- Sunglasses for Derby Day: Call Back Sunglasses
- Umbrella for the Kentucky Derby: Rain or Shine Umbrella-Dreamer
- Floral Derby Necklace: Your Favorite Printed Flower Necklace
- Kentucky Derby Gloves: Carolina Amato Farfalla Gloves
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 these pieces for the Derby!
Ann Taylor Ruffle Halter Top
- Description
- Pros
What Customers Say: ‘The color is a perfect pink and the fabric is really nice. Can be worn with anything and will be great for spring and summer. It runs on the small side. Generally AT runs a big large but not this piece.’
- Stand collar with ties
- Sleeveless
- Lined
Marina Joy Silk Maxi Dress
- Pros
- 70% Cotton 30% Silk
- V-neckline
- Capped sleeves
The Gold Dust
- Pros
- 94% Polyester, 6% Spandex
- Not itchy! NOT made of actual glitter or sequins, but printed polyester to look like it
Pastels for the Kentucky Derby
If pastel hues are more your style, we’ve got the perfect styles for the Kentucky Derby! From Ann Taylor dresses to striped polos, shop these looks to find your perfect Derby wear.
Short Sleeve Flare Dress
- Description
- Pros
What Customers Say: ‘Beautiful and flattering dress that is perfect for springtime.’
- Crew neck
- Short sleeves
- Hidden back zipper with hook-and-eye closure
- Lined body
The Savannah Swinger
- Description
- Pros
What Customers Say: “We are the youngest living in a 55+ community & we love to push boundaries at the events (which are actually damn fun!) I got this dress for me & the matching pants/bow tie for my hubby. We stuck out like sore thumbs at the Derby Party and THAT, my Shinesty compadres, was the goal & we nailed it. Great fit, too!”
- 97% Polyester 3% Spandex
- Adjustable straps
- Tie closure
- Two on seam pockets
Sonora Stretch Terry Pant
- Pros
- Belt loops
- Hidden zip fly with top button closure
Women's Chalk Pink V-Neck
- Description
- Pros
What Customers Say: ‘So soft! The color is perfect and it fits exactly as described!’
- Made with StratuSoft, our super soft cotton-poly fabric blend
- High-quality material that washes well and doesn’t wrinkle easily
- Preshrunk and semi-fitted for a timeless, relaxed look
Patterns and Prints for the Kentucky Derby
The Kentucky Derby is the perfect place to show off your best patterns and printed styles. Shop some of our favorites from pattern experts like Johnny Was and Shinesty!
Presley Crop Button Down Top
- Pros
- Slouchy cropped silhouette
- Elastic hem
Renata Floral Front Twist Button-Up Top
- Pros
- 100% Lyocell
- Button-up top
- Vibrant floral print
The Porch Swing
- Description
- Pros
What Customers Say: “Dress is very cute, fits the occasion I ordered for. Company is great to deal with, timely shipping, quality product.”
- 97% Polyester 3% Spandex
- Blue and white wicker pattern perfect for Derby Day
Voluminous Styles for Derby Day
If you love going over the top with your fashion choices, Derby Day is the day to do so! We love these exaggerated sleeve styles, but don’t feel limited to them. Feel free to play with loud prints, colors, and other exaggerated fashion features for the Kentucky Derby.
Mare Mare Puff-Sleeve Off-The-Shoulder Mini Dress
- Description
- Pros
What Customers Say: “This is one of the most versatile dresses in my closet. Love the bright white color. The shoulders hit just right and does not rise like most off the shoulders styling. The fabric feels comfortable and love the fullness. I am looking forward to the many looks this dress will give this summer.”
- Three fabulous color choices
- Polyester; polyester, elastane lining
- Pullover styling
Arianne Elmy Good Luck Dress
- Description
- Pros
What Customers Say: “I ordered this dress to wear to my 60th birthday celebration….to say I got compliments is a complete understatement….I’ve been a ‘Free People’ girl since 2019….I’ve ordered numerous items, all to my complete satisfaction…..But this dress is my favorite!!!!!…..”
- Four color choices
- Super exaggerated sleeves
- Stunning embroidery
Pleated Halter Flare Dress
- Description
- Pros
What Customers Say: ‘Perfect fit, beautiful color. Perfect for a brunch or early dinner party.‘
- 100% Polyester
- Tiered at the skirt for next-level comfort
- Shirred halter neck with front slit
- Hidden back zipper with hook-and-eye closure
- Lined
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.
Crown Vintage Felt Panama Hat
- Description
- Pros
What Customers Say: ‘I am glad I purchased this hat. I’ve gotten several compliments, already. It fits comfortably too.’
- Structured design makes it a sophisticated piece
- Decorative tie around the base for a chic touch
- Wide brim that fully covers your face and eyes
Kelly & Katie Chainlink Fedora
- Pros
- Structured hat features a woven design
- Eye-catching metal detail
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.
Floral Statement Sandals
- Pros
- Open toe
- Padded footbed for complete comfort
- 2" heel
Vince Camuto Faiza Sandal
- Pros
- 1.8" Heel
- Open Square Toe
- Padded Footbed
- Slip On
Journee Collection Melissa Sandal
- Description
- Pros
What Customers Say: ‘Perfect mule. True to size. I also tried the wide because sometimes shoes like this are tight on me but this fit is JUST RIGHT.’
- Slip-on
- Square open toe
- Padded footbed
- 4" covered block heel
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.
Carrie Convertible Clutch
- Description
- Pros
What Customers Say: ‘This is my second one! It’s extremely roomy in that it holds all of my grocery and store cards plus credit cards and driver’s license! There is a zippered inside pocket for loose coin and places fir bills. The purse also have several pockets plus a magnetic snap pocket. Yes, all this room in a beautiful small rectangular purse that I use with the detachable shoulder strap. The quality is wonderful. It’s well made and looks wonderful It’s durable yet very attractive. I receive many compliments on it.’
- Pebbled, full-grain leather
- Natural faille lining
- Zipper closure
Carter Gemstone Bracelet
- Pros
- 6 1/4" interior diameter
- Genuine mother of pearl measures 3/16"
- Available in 18k gold plated brass
The Radiator e.w. Emerald
- Pros
- Lobster closure
- 16-18" in length
- Stunning 1.5 carat center stone
Call Back Sunglasses
- Pros
- TAC Polarized Lens with Maximum Optical Clarity
- Anti-Glare, Scratch-Resistant, Impact-Resistant
- 100% UVA/UVB Protection plus Blue Light Blocking!
Rain or Shine Umbrella-Dreamer
- Pros
- Can be used as a shield from the rain and shade from intense sunlight
- Adds a touch of femininity to a classic staple accessory
Carolina Amato Farfalla Gloves
- Description
- Pros
What Customers Say: “These satin gloves were the icing on the cake…and a must have accessory for the best photo ops!”
- 11" long
- Silk, spandex
- Elegant bows top these silky gloves
Want to rent your Kentucky Derby styles instead? Shop Nuuly’s Spring closet for the best ideas!
Need alcohol for Derby Day?
What would a Kentucky Derby party be without a Mint Julep? Find alcohol near you with Saucey or Minibar and have the bourbon of your choice delivered right to your door.
Need even more shopping? Keep reading!
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