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What I’d wear to the 2026 Kentucky Derby
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items Get race-day ready with the prettiest Kentucky Derby fashion finds! I am a Louisville native and have been around for over 20 derbies. Here is what I would wear to celebrate the most exciting 2 minutes in sports! 🏇
Sections
2
Hats & Fascinators
Shoes
Hats & Fascinators
The wider the brim = the better! Listen, Derby is no time to shy away. How many opportunities do you have to wear a chic hat!!
Women's Wide Brim Flower Sinamay Wedding Kentucky Derby Church Hats (196419489)
In my eyes, fascinators = Oaks & hats = Derby. This fascinator, however, I think could be styled for either occasion. It’s very chic in design & I’m obsessed with the butter yellow.
Butter Yellow Large Brim Sinamay Boater Fascinator Hat Base for Millinery & Hat Making
The texture is different from any other hat or fascinator I have seen! Definitely eye catching
Mint Green Kentucky Derby Hat Spring wedding guest Fascinator Floral Special Event Headpiece for Garden Parties, Royal Ascot Race Day Outfit
Big brim, big bow, and pink?! My trifecta!!!
Pink Wide Brim Sinamay Hat With Convertible Bow, Kentucky Derby Ascot Royal Wedding Church Garden Party Mother of the Bride Hat - Etsy
Ooh this is a favorite. What a cool design. I haven’t seen a hat with a design underneath the hat!
M95( White/Black Polka )Kentucky Derby Hat, Church Hat, Wedding Hat, Easter Hat, Polka Dot hat, Big Bow, Wide Brim Sinamay Hat
Organza AND polka dots?! My dream!! Organza is a beautiful and feminine fabric when looking for a hat. And I love the vintage feel the polka dots bring.
Ivory Organza Kentucky Derby Hat Polka Dot Cream Hat Bow Dress Hat Garden Party Fascinator Wedding Guest Hat Summer Formal Hat Tea Party Hat
Some hats and fascinators can look silly to me. This one is very chic and sophisticated. It’s bold but still makes a statement.
Quinn Fascinator
The netting on this one is a beautiful feature. I am a huge baby blue fan too.
Baby Blue Fascinator Hat: Feathers & Net, Wedding Guest Headpiece
I LOVE the birdcage netting!!! If you are a bride with a derby bach/bridal shower this is a must!
Bride wedding hat with veil white - Kentucky derby hat for women - Royal Ascot hat white - bridal veil hat with crystals engagement party
What better way to celebrate a run for the roses than with a fascinator that has roses?
Large Red Rose Flower Feather Teardrop Fascinator Hat Headband Races Wedding Floral Big Headpiece 7194
The bigger that hat/fascinator = the better!!
Feather Fascinator Hat for Women – Kentucky Derby & Royal Ascot Style Mesh Headpiece
I love the structure of this one! The bow and beautiful shade of blue give a feminine balance to the hat.
M23156 (Light blue White hat)Medium Flat-brim Sinamay Fascinator hat for Kentucky Derby hat, Church hat, Wedding hat, Easter hat, Ascot hat
Shoes
These are so cute and they look pretty comfy. Shoutout to Belk, these are on sale and are $100 (yes you read that right) off!! Def a steal
Kady Sandals
How darling are these gingham heels? Bring on all the spring vibes
Antonio Melani x Amanda Jones Vaughan Penny Gingham Platform Block Heel Slingback Pumps | Dillard's
Betsey Johnson are the best!!!! How fun are these sling backs? For a day at the tracks I would opt for a comfier heel. It’s a long day on your feet. But don’t feel like you have to sacrifice style for comfort!
Betsey Johnson Avi Pump
Like I said, it’s a long day on your feet. A pair of comfy flats may be the thing for you. Or you could always bring them to change into.
The Bow Point II in Conch | Women's Flats | Rothy's
Oaks or Derby, if it doesn’t rain at one event, it will probably rain at the other. I don’t make the rules,sorry! I was at the derby a few years ago and it was down pouring. There have also been plenty of beautiful derby days. Be sure to check the we...
Women's Original Tall Rain Boots
I’m loving the fun pearl detailing on this one! There are plenty of elements to bring your outfit together with these darling sandals.
Alex Marie Johanna Floral Brocade Pearl Embellished Block Heel Dress Sandals | Dillard's
The feathering detail fits all the derby vibes. So cute!
Women's Jace Heel Sandal in Soft Fern Satin Fabric | Sam Edelman