Best Dresses for the Kentucky Derby in September 2020

• The Hatista
• Outfits
• February 9th 2019 / Updated: June 30th 2020

The most important element of your Kentucky Derby outfit is of course the Hat, but you can't wear just a Hat!. You do need wear a Dress, Jumpsuit, or Suit also folks, so this post is about the best dresses I've found for you. Don't worry I'm a Milliner so I've not ignored hats - they can be found in my post about those.

For more inspiration, style advice, and full outfits including the all important headwear, shoes and accessories then do be sure to read my Blog Spot on Kentucky Derby Outfits.

You have two choices you can go with on the dress (Heavy Florals, or Single Colour Dress) Stripes or Polka Dot can also be very on point if dressed with suited hats. If you go for a heavy floral pattern, remember you will need find a hat to match. The best (most Derby Hats) are dressed in ample flowers, so your dress could be ample in flowers that match. Or, keep the dress a single colour (probably a bright) and you can go all out on your Kentucky Derby Hat so that the hat grabs all the attention, while the dress harmonizes it. Stick with colors that remind you of Summer.

The most appropriate hem lengths by far are on the knee, just above knee, or mid calf. 50's Style A Line, pinched at the waist are super popular for the Derby, and flatter almost all body shapes. A Bardot neckline is also super popular at the moment. The Red Rose has been the official flower for Kentucky Derby since 1904, so Dresses in Red are always popular and encouraged, but not an essential.

To help you find the perfect Derby dress, I've picked loads out for you below, offering a variety to suit a wide range of budgets. Whether you are looking for the Ultimate Designer Dress, or 'Just need a dress', below you should find the perfect Kentucky Derby dress for you.

This post includes affiliate links - suggestions of items I've selected you. If you see anything you like, click the links and decide to buy the suggestion, then the retailer will give me a little commission (maybe even enough to buy a Julep) to thank me.

Theme of the Day - Derby Day, Oaks Day?

The Red Rose has been the official flower for Kentucky Derby since 1904 - "Garland of Roses". Each year, a garland of more than 400 red roses is sewn into a green satin backing with the seal of the Commonwealth on one end and the Twin Spires and number of the race's current renewal on the other, and is draped over the winning horse. You don't HAVE to dress in a Garland of Roses, but many will choose to encorporate this flower in their outfits.

For Oaks Day you should think pink - "Lillies for the Fillies". The Stargazer Lily has been the official flower of the Oaks since 1991, when the Kroger Co. was asked to craft a feminine garland for the winning filly in the Derby’s sister race. The stargazer lily was picked to represent femininity and strength. Follow the theme in pink outfits, and hats with the beautiful big pink and white lillies.

1. "It's the Party of the Century, a really big deal, and will prob be one on many many, so I'll invest in one that should last a lifetime."

Below is a gallery of some luxury Kentucky Derby dresses I've hunted out for you to splash out on.

2. "I'll probably get good use from it again and again for a few seasons, or weddings, so don't mind spending a little bit on my dress, but I'll need buy drinks when I get there, so don't leave me broke!!"

Below is a gallery of some perfect Kentucky Derby dresses, that offer good 'cost per wear' if you are wearing for a few parties, but certainly not as expensive as the aspirational -for most- ones above.

3. "It's a one off Event / Party. Just looking for an outfit that is on theme, but won't cost the earth."

Below is a gallery of some pretty, and stylish Kentucky Derby dresses available on a High Street Budget, and won't leave you feeling like you can't now afford to buy the Juleps.