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Classy Kentucky Derby Outfits for Women Over 50

Embrace Derby Day with these fashionable looks!


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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 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

Bright Derby Top

Buy from Ann Taylor, $56

Features You'll Love

  • Stand collar with ties
  • Sleeveless
  • Lined

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.”

Significant Other Strapless Midi Dress

Anthropologie Dress for the Kentucky Derby

Buy from Anthropologie, $428

Features You'll Love

  • Viscose, linen
  • Cotton lining
  • Zipper styling

Marina Joy Silk Maxi Dress

Maxi Dress for the Kentucky Derby

Buy from Johnny Was, $578

Features You'll Love

  • 70% Cotton 30% Silk
  • V-neckline
  • Capped sleeves

The Gold Dust

Womens Gold Glitter Print Suit Jacket

Buy from Shinesty, $70

Features You'll Love

  • 94% Polyester, 6% Spandex
  • Not itchy! NOT made of actual glitter or sequins, but printed polyester to look like it

Air Polo

Crisp White Polo

Buy from Tasc $68

Features You'll Love

  • Two buttons at the collar
  • Two side splits
  • Soft, lightweight fabric

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.”

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

Pastel Ann Taylor Dress for the Derby

Buy from Ann Taylor $149

Features You'll Love

  • Crew neck
  • Short sleeves
  • Hidden back zipper with hook-and-eye closure
  • Lined body

What Customers Say: “Beautiful and flattering dress that is perfect for springtime.”

The Savannah Swinger

Plaid Strappy Dress for the Kentucky Derby

Buy from Shinesty $80

Features You'll Love

  • 97% Polyester 3% Spandex
  • Adjustable straps
  • Tie closure
  • Two on seam pockets

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!”

Sonora Stretch Terry Pant

Comfortable Women's Pants for the Derby

Buy from Flag & Anthem, $70

Features You'll Love

  • Belt loops
  • Hidden zip fly with top button closure

Women’s Chalk Pink V-Neck

Pastel V-Neck for the Kentucky Derby

Buy from Fresh Clean Threads, $22

Features You'll Love

  • 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

What Customers Say: “So soft! The color is perfect and it fits exactly as described!”

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!

Daphne Silk Maxi Dress

Floral Print Dress for the Derby

Buy from Johnny Was, $598

Features You'll Love

  • Split neckline
  • Smocking at the sleeves
  • Fitted elastic waist leading to a tiered maxi skirt with intricate detailing

Presley Crop Button Down Top

Women's Button Down for the Kentucky Derby

Buy from Kut from the Kloth $63

Features You'll Love

  • Slouchy cropped silhouette
  • Elastic hem

Renata Floral Front Twist Button-Up Top

Floral Top for Derby Day

Buy from Kut from the Kloth, $79

Features You'll Love

  • 100% Lyocell
  • Button-up top
  • Vibrant floral print

The Porch Swing

Light Blue Caned Wicker Wrap Dress for the Kentucky Derby

Buy from Shinesty, $60

Features You'll Love

  • 97% Polyester 3% Spandex
  • Blue and white wicker pattern perfect for Derby Day

What Customers Say: “Dress is very cute, fits the occasion I ordered for. Company is great to deal with, timely shipping, quality product.”

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

Puffy Sleeve Top for the Kentucky Derby

Buy from Anthropologie, $158

Features You'll Love

  • Three fabulous color choices
  • Polyester; polyester, elastane lining
  • Pullover styling

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.”

Arianne Elmy Good Luck Dress

Puffy Long Sleeve Derby Dress

Buy from Free People, $360

Features You'll Love

  • Four color choices
  • Super exaggerated sleeves
  • Stunning embroidery

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!!!!!…..”

Pleated Halter Flare Dress

Halter Dress for Derby Day

Buy from Ann Taylor, $189

Features You'll Love

  • 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

What Customers Say: “Perfect fit, beautiful color. Perfect for a brunch or early dinner party.

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.

Sun Drench Felt Hat

Yellow Women's Derby Hat

Buy from Free People, $98

Features You'll Love

  • Round brim style
  • Dipped crown
  • Defined ribbon at center

Crown Vintage Felt Panama Hat

White Hat for the Kentucky Derby

Buy from DSW, $30

Features You'll Love

  • 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

What Customers Say: “I am glad I purchased this hat. I’ve gotten several compliments, already. It fits comfortably too.”

Kelly & Katie Chainlink Fedora

Women's Fedora for the Kentucky Derby

Buy from DSW, $30

Features You'll Love

  • 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

Statement Sandals for Derby Day

Buy from Ann Taylor, $158

Features You'll Love

  • Open toe
  • Padded footbed for complete comfort
  • 2″ heel

Vince Camuto Faiza Sandal

Pastel Sandals for the Kentucky Derby

Buy from Vince Camuto, $99

Features You'll Love

  • 1.8″ Heel
  • Open Square Toe
  • Padded Footbed
  • Slip On

Carina Cross Strap Mule

Women's Mules for Derby Day

Buy from Nisolo, $90

Features You'll Love

  • 3″ heel
  • High-quality, breathable leather upper, lining, and outsole
  • Cushioned, shock-absorbing insole
  • Soft, interior leather lining

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.”

Journee Collection Melissa Sandal

Heeled Sandals for the Kentucky Derby

Buy from DSW, $50

Features You'll Love

  • Slip-on
  • Square open toe
  • Padded footbed
  • 4″ covered block heel

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.”

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

Purse for the Kentucky Derby

Buy from Levenger, $160

Features You'll Love

  • Pebbled, full-grain leather
  • Natural faille lining
  • Zipper closure

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.”

Carter Gemstone Bracelet

Bracelet for Derby Day

Buy from Gorjana, $45

Features You'll Love

  • 6 1/4″ interior diameter
  • Genuine mother of pearl measures 3/16″
  • Available in 18k gold plated brass

The Radiator e.w. Emerald

Chunky Deco Inspired Bezel Set Pendant

Buy from Frank Darling, $1,400

Features You'll Love

  • Lobster closure
  • 16-18″ in length
  • Stunning 1.5 carat center stone

Call Back Sunglasses

Sunglasses for Derby Day

Buy from Privé Revaux, $50

Features You'll Love

  • 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

Umbrella for the Kentucky Derby

Buy from Johnny Was, $98

Features You'll Love

  • Can be used as a shield from the rain and shade from intense sunlight
  • Adds a touch of femininity to a classic staple accessory

Your Favorite Printed Flower Necklace

Floral Derby Necklace

Buy from Free People, $38

Features You'll Love

  • Defined floral pendant
  • Versatile side strings
  • Two great color choices

Carolina Amato Farfalla Gloves

Kentucky Derby Gloves

Buy from Anthropologie, $127

Features You'll Love

  • 11″ long
  • Silk, spandex
  • Elegant bows top these silky gloves

What Customers Say: “These satin gloves were the icing on the cake…and a must have accessory for the best photo ops!”

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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