It feels so surreal that it’s already Kentucky Derby time here in Louisville after last year’s weirdness with Derby in September and limited spectators. The majority of the big parties and festivities were still scaled back or virtual this year, so the energy of the social event of the year in this area is off. Yet, people ARE going this year in a much bigger way than allowed last year and I can’t wait to see the fashion! I have a feeling people are going to go extra-extra, which is exactly what I want to do after being cooped up in athleisure for over a year.

While I have no plans on attending Oaks or Derby this year, I did some virtual outfit planning as every year I seem to get asked for ideas. A lot of Kentucky Derby fashion editorials are missing plus size bodies, so finding inspiration can be difficult if you’re not quite sure what you’re looking for. The good thing about Derby is that the style recipe doesn’t really change – that’s the fun of tradition. So, if you like these and want to use for future inspiration, please pin them for later!

What to wear to the Kentucky Derby?

Here’s a link if you want to see some of my past years’ Kentucky Derby Outfit posts.

This is what my friend Nanci and I wore to Derby 2019. I usually prefer a fascinator because it’s difficult to find a hat that is large enough to fit my big head, ha! I loved Nanci’s big hat and black and white outfit that stood out against all the bright colors people had on that day.

I was (and still am) obsessed with off-the-shoulder dresses, as seen in this opening night photo during Derby week – about 5 days before the photo above:

Off-the-shoulder or not, there are so many different options on what to wear. Wear pants, a jumpsuit, a dress – whatever makes you feel great! With the exception of denim – some seating areas are a no-denim zone so you’ll want to check that in advance if that’s the route you want to take.

Kentucky Derby Outfit Ideas

Here are some fun ideas I put together for this year’s Kentucky Derby. I had to stop myself from putting more together because I looked up at the clock and didn’t know where the time went! All headpieces below are by local Louisville duo, The Hat Girls.

Blue Eyelet Dress
Strappy Open Toed Heels (wide width)
Yellow Crossbody Bag
Pale Blue Fascinator
Stud Earrings

Bright and cheery Kentucky Derby outfit idea

Textured Shift Dress
Orange and Pink Fascinator
Double Stud Earrings
Braided Slide with Block Heel (wide width)
Tote Bag

Separates with lace and florals

Stand Collar Blouse
Eyelet Lace Skirt
Vegan Leather Pouchette with Chain
Wrap Wedge Sandal
Jeweled Studs

Neutral jumpsuit with pops of color

Wide Leg Lace Jumpsuit
Asymmetric Pearl Earrings
Slingback Sandal
Orange Silk Fascinator
Beaded Clutch

Tips for Kentucky Derby Planning

Here are a few tips for things to be prepared for if you’re coming to the Kentucky Derby:

• Weather: The weather is super unpredictable on the first Saturday of May. Make sure to triple check the weather for the temperature, knowing you may need to layer up or lighten up. Also, take a poncho. It doesn’t take up much space, and I promise you’ll be so happy you have it when it downpours – as it often does. (see evidence below)
• Feet comfort: I applaud those of you who can strut in heels all day. I will never be one of you! If you’re someone who can handle heels a few hours and thinks that Derby day is the time to bust out the fanciest, highest ones, you may want to reconsider. Unless you have very special access to parking or are being chauffered in, you will face a hike from your car to the entry. Once you’re inside, it’s a very long day standing – even if you have seating. You’ll want to walk around and people watch, get drinks, go to the Paddock. Just be prepared – I’ve seen many, many people end up barefoot by the end of the day, and that’s just not the way! A wedge offers a little more support, or you can go with flats.
• Handbag: A tiny handheld clutch seems like a cute idea, but hanging onto it all day without a strap is a pain, especially if you’re trying to juggle your racing program and mint julep. Or figuring out what to do with it in a bathroom stall. Consider a bag with a strap. Even better, one with a crossbody strap.
• Earrings and Mask: For 2021 with a mask requirement, consider the type of earrings you are going to wear. I love huge statement earrings, but those + a mask up and down to eat and drink is a bad idea. Consider large studs and make sure to test out if your mask is going to get caught on them.
• Battery charger: If you plan on taking a lot of photos or video, consider carrying an extra charging pack. It’s a long day, and you don’t want to run out of juice.
• Hat or fascinator weight: I am all for anyone who wants to wear the biggest hat ever seen at the Derby. I just suggest that you consider the weight and security of the hat or fascinator and how it will hold up throughout the day. It’s no fun to readjust it all day, and can definitely feel really heavy after 8+ hours.

Questions about race day dressing? Let me know in the comments!