The Kentucky Derby is the preppy fashion event of the spring. No matter if you’re watching the race in Louisville or hosting a Derby-themed party, the key to any fabulous Derby event is dressing the part.

It’s almost that time again… Getting out your better than Sunday’s dress and let’s hit the races! Two years ago, I found some great dresses for Derby and Steeplechase that looked amazing with my hat, that a friend of mine made me, pictures here and here. This year, I found a dress from Ann Taylor and it is absolutely perfect, it’s part of their new Spring collection. Before you head to one of these events make sure you have a few things:

The perfect novelty bag. This is just as important as finding the perfect hat! A place that is well known for their elaborate novelty bags is kate spade. Every month they come out with a new theme and you will also find a new novelty bag as well.

The perfect Spring dress. There are two schools of thought regarding Kentucky Derby and Steeplechase dresses: some attendees want to let their hats shine, so their dresses remain simple. But others want their dresses to be the main event, so they’ll choose a subtle hat to pair with a brightly colored or patterned dress instead.

Since Derby Day is all about channeling your inner Southern Belle, it’s essential to incorporate bright colors, fun florals, or a classic print. I have picked out a few styles below: daisy garden poplin dress, one shoulder ruffle dresspom embroidered dress, hibiscus ruffle neck dress, and vintage floral dress.

Block Heels. Chic summer sandals, open-toed heels, or a chunky pair of espadrilles will do the trick on Derby Day. While the actual Derby race only lasts a few minutes, the day as a whole is quite lengthy. I prefer the block heel shoe, which is a must-have if you are in the infield you will be glad you did, so your heel is not sinking into the grass continuously or just for comfortable height.

The perfect hat. No Derby outfit is complete without a hat. While wide-brimmed hats are the most popular style, there’s really no limit to how creative your headwear can get. Fascinators have also become popular at Derby and Steeplechase in recent years as well.

To some, the Kentucky Derby is known as “the most exciting two minutes in sports,” but we think it’s “the most exciting headwear in fashion” is more fitting. Let’s be real, some people start with the hat and then find the dress later. This year, that’s what I did. I started searching on websites early and stumbled upon this facilitator hat. Later to find, when I started searching for a dress I realized I had one the whole time.


The final step in your Derby dressing process: accessories. Since the hat and dress are the center of the outfit, keep the accessories to a minimum. Choose simple, subtle jewelry.

Shop the look below:

Dress: Ann TaylorAnn Taylor|| Shoes: Ann Taylor || Bag: kate spade|| Hat: Etsy

Thanks for viewing my blog.


Signature AHK

Posted by:Ashley Holford

Nashville Blogger sharing and doing what I love, "Inspiring others".

One thought on “Derby/Steeplechase Season

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s