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Classy Kentucky Derby Outfits for Women Over 50
Find your perfect Kentucky Derby style!
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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!
Bright Derby Top
Ann Taylor Ruffle Halter Top
Buy from Ann Taylor:$56
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
Anthropologie Dress for the Kentucky Derby
Significant Other Strapless Midi Dress
Description
Pros
Viscose, linen
Cotton lining
Zipper styling
Maxi Dress for the Kentucky Derby
Marina Joy Silk Maxi Dress
Buy from Johnny Was:$578
Pros
70% Cotton 30% Silk
V-neckline
Capped sleeves
Womens Gold Glitter Print Suit Jacket
The Gold Dust
Buy from Shinesty:$70
Pros
94% Polyester, 6% Spandex
Not itchy! NOT made of actual glitter or sequins, but printed polyester to look like it
Crisp White Polo
Air Polo
Buy from Tasc:$68
Description
Pros
What Customers Say: "Beautiful fabric, great fit, and stylish, too. I’m NOT a polo shirt kinda gal, and even I can admit it looks fabulous on me."
Two buttons at the collar
Two side splits
Soft, lightweight fabric
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.
Pastel Ann Taylor Dress for the Derby
Short Sleeve Flare Dress
Buy from Ann Taylor:$149
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
Plaid Strappy Dress for the Kentucky Derby
The Savannah Swinger
Buy from Shinesty:$80
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
Comfortable Women's Pants for the Derby
Sonora Stretch Terry Pant
Buy from Flag & Anthem:$70
Pros
Belt loops
Hidden zip fly with top button closure
Pastel V-Neck for the Kentucky Derby
Women's Chalk Pink V-Neck
Buy from Fresh Clean Threads:$22
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!
Floral Print Dress for the Derby
Daphne Silk Maxi Dress
Buy from Johnny Was:$598
Pros
Split neckline
Smocking at the sleeves
Fitted elastic waist leading to a tiered maxi skirt with intricate detailing
Women's Button Down for the Kentucky Derby
Presley Crop Button Down Top
Buy from Kut from the Kloth:$63
Pros
Slouchy cropped silhouette
Elastic hem
Floral Top for Derby Day
Renata Floral Front Twist Button-Up Top
Buy from Kut from the Kloth:$79
Pros
100% Lyocell
Button-up top
Vibrant floral print
Light Blue Caned Wicker Wrap Dress for the Kentucky Derby
The Porch Swing
Buy from Shinesty:$60
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.
Puffy Sleeve Top for the Kentucky Derby
Mare Mare Puff-Sleeve Off-The-Shoulder Mini Dress
Buy from Anthropologie:$158
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
Puffy Long Sleeve Derby Dress
Arianne Elmy Good Luck Dress
Buy from Free People:$360
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
Halter Dress for Derby Day
Pleated Halter Flare Dress
Buy from Ann Taylor:$189
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.
Yellow Women's Derby Hat
Sun Drench Felt Hat
Buy from Free People:$98
Pros
Round brim style
Dipped crown
Defined ribbon at center
White Hat for the Kentucky Derby
Crown Vintage Felt Panama Hat
Buy from DSW:$30
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
Women's Fedora for the Kentucky Derby
Kelly & Katie Chainlink Fedora
Buy from DSW:$30
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.
Statement Sandals for Derby Day
Floral Statement Sandals
Buy from Ann Taylor:$158
Pros
Open toe
Padded footbed for complete comfort
2" heel
Pastel Sandals for the Kentucky Derby
Vince Camuto Faiza Sandal
Buy from Vince Camuto:$99
Pros
1.8" Heel
Open Square Toe
Padded Footbed
Slip On
Women's Mules for Derby Day
Carina Cross Strap Mule
Buy from Nisolo:$90
Description
Pros
What Customers Say: "The sandals are comfortable and practical for wear. Heel height is just right as I like extra cushioning in the heels. I usually do not wear ballet flat-type sandals due to the cushioning/padding being so thin, but I do need sandals to wear in the warmer months. The color is fitting to my skin tone and pairs well with most clothes because it is a neutral color. Definitely read other reviews and the entire product description prior to buying to ensure I purchase the right size and product for my needs."
3" heel
High-quality, breathable leather upper, lining, and outsole
Cushioned, shock-absorbing insole
Soft, interior leather lining
Heeled Sandals for the Kentucky Derby
Journee Collection Melissa Sandal
Buy from DSW:$50
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.
Purse for the Kentucky Derby
Carrie Convertible Clutch
Buy from Levenger:$160
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
Bracelet for Derby Day
Carter Gemstone Bracelet
Buy from Gorjana:$45
Pros
6 1/4" interior diameter
Genuine mother of pearl measures 3/16"
Available in 18k gold plated brass
Chunky Deco Inspired Bezel Set Pendant
The Radiator e.w. Emerald
Buy from Frank Darling:$1400
Pros
Lobster closure
16-18" in length
Stunning 1.5 carat center stone
Sunglasses for Derby Day
Call Back Sunglasses
Buy from Privé Revaux:$50
Pros
TAC Polarized Lens with Maximum Optical Clarity
Anti-Glare, Scratch-Resistant, Impact-Resistant
100% UVA/UVB Protection plus Blue Light Blocking!
Umbrella for the Kentucky Derby
Rain or Shine Umbrella-Dreamer
Buy from Johnny Was:$98
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
Floral Derby Necklace
Your Favorite Printed Flower Necklace
Buy from Free People:$38
Pros
Defined floral pendant
Versatile side strings
Two great color choices
Kentucky Derby Gloves
Carolina Amato Farfalla Gloves
Buy from Anthropologie:$127
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.
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