What to wear for the Kentucky Derby? Tips and Outfit Ideas

• The Hatista
• Fashion Post
• March 12th 2020 / Updated: September 27th 2020

Once you have your tickets booked, start planning your outfit right there and then! The shops start stacking their racks with Summer Fashions from February, and online retailers have summer wear all year round, so start planning now. PLEASE, as a Milliner I ask you, “Don’t leave until end April to hectically throw something together and get delivered in time.

The most important element of your Kentucky Derby or Oaks Day outfit is the Hat, and there is a high probability that your perfect Hat will need be handmade to order, with a few weeks MINIMUM to be made." You are likely going to be buying from Overseas (the widest selection of Racing Fashion Hats are by UK or Australian Milliners, where Millinery is worn more often). So, please make sure you plan ahead in time for production and delivery. The other great thing about doing this is that you allow the Milliner to make customization's for you, specific for your outfit. Almost all Etsy, or other independent sellers will work with you to make such customization's. Your Derby outfit can be fun and full of character, less matchy matchy than a Mother of the Bride or wedding guest outfit would be. Don’t be afraid to get creative with your color accents, and build a punchy outfit you wouldn’t normally wear for a formal event. Below are my style tips on how to pull together your Kentucky Derby Day, Oaks Day or Derby Party outfits. For DOZENS of more dresses only, then do be sure to read my Blog Spot on Kentucky Derby DRESSES.

This post includes affiliate links - suggestions of items I've hunted out on the Internet for 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 latte) to thank me.

Pick the Jaw-dropping Hat of Your Dreams First

Yes, I’m a Milliner, so you may think I’m bias! But honestly it’s so much easier to find a dress to go with an already chosen Hat, than to go out and find a hat for a chosen dress. There are zillions and zillions of dresses to choose from across Stores and the Internet but significantly less hats – The Derby is all about the Hat, so find the Hat of your dreams first, without being in the limitations of the dress, and you will be able to find a dress afterwards for sure – I promise.

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 incorporate 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.

Monochromatic Black and White - Classic Racing Fashion

Monochrome outfits are my very favorite for Racing. You can nearly never fail to look divine at the races in a Monochromatic outfit. Black and White works great on all skin tones, so there are always zillions of outfits you can choose in this colour combo.

For the hat, choose the majority color according to your hair color. If you are blond, then a black base will contrast better. If you are dark haired then the opposite. If you are a red-head then either will contrast great.

Monochromatic Black and White - with "Color Pop"

Find the all black and white a little unadventurous for a vibrant Derby Day outfit? Want to go a little brighter, then add a color pop to the classic monochromatic outfit.

Almost any bright will work. Orange looks great popped on a black and white striped, gingham, or polka dot outfit, but by far the most popular color pop to a monochromatic racing fashion look is red. For any race day this is true, and for many decades, but especially for the Kentucky Derby. You want to celebrate the 'Run for the Roses'.

Multi Tone Pastels

One of the most alluring and popular ways to dress for the Derby is in Pastels.

It’s fun to wear pastels with darker, or brighter shades of the same colour to create a monochromatic style. By pairing bright and pastel shades of a colour in your outfit, you’ll add personality, and not look washed out, or like you are headed to the Easter Parade.

Current Trend Golden Yellow

First Amal Clooney wore all over yellow for the Wedding of the Year on the 19th May, and then Meghan Markle decided to copy her wedding guest and switch her neutrals to cheery yellow during her Royal outing in London in June. July, for the Mens Wimbledon Final Kate Middleton Duchess of Cambridge wore a Dolce & Gabbana Yellow shift dress. Now, it seems everyone is looking for ways to wear this cheery hue.

Yellow is a happy colour. Worn all over for a wedding would be to in your face and attention seeking, but perfect for the Kentucky Derby. Grab the attention and show off your playful side, with this standout Racing Fashion look.

Below are a few Yellow outfits. For more tips on wearing this cheery hue, read my Blog Spot on How to Wear Yellow.

Bold Floral Prints Brights or Pastels

You can’t go wrong with a sophisticated Floral Dress for the Kentucky Derby, matched with a complimenting large hat, headpiece or fascinator that is of course an essential for your Kentucky Derby outfit. Solid colors, color blocked look great for racing outfits, but, I personally find simple lines and colors worn with big headpieces are more for Royal Ascot. The Kentucky Derby, is more florals in either bold prints or sweet pastels like Mint, Baby Pink, Cornflower / Serenity Blue and Pastel Lilac.

On Trend - Pantone Living Coral

Coral instantly brings excitement to an outfit for the Races.

A great way to let the bold tones of Coral stand out without competing with any other pieces in your outfit, is to pair coral with nude or grey neutrals (including Gold or Silver). Your look will be clean and refined, but fun and punchy. Coral is great for adding a touch of cheerfulness and lifts your spirits.

This colour combination is perfect if you are afraid that all over coral, even if mixed tones, will be to bright. Both dark and light neutral shades team well with coral.

For more ideas on wearing this years Color of the Year - Living Coral - you can also read the post on How to Wear Coral.

Coral and Clean White

This won't be the first year you will see Coral at the Kentucky Derby, as it's a colour that's been in peoples wardrobes for about 10 years, but you definitely will be seeing even more of it since 2019. Coral and White floral outfits are perfect for the Kentucky Derby. Coral is a pretty colour, but also bright. Wearing with lot's of white stops you looking like a bright flame walking around, while the high contrast on the clean white lets the pretty coral elements shine their best. The fascinator and dress in the below outfit aren't by the same designer, but how perfect are they together?? It's as if the Milliner and dress designer collaborated over lunch!!

Two Trends, One Outfit

I love the fashion-forward combination of a mixing your hues, for a day at the races.

The pastels trend is going nowhere fast, but going all pastels is something most of us haven't attempted since we were 10 years old. Pastels work brilliant with Florals, where you can find multi tonal floral pieces. The outfit below brings in regal purple, ultra violets, and pastels. A winning combination for a Kentucky Derby or Royal Ascot Ladies Day outfit idea.

Some Other Fabulous Dresses and Accessories I've found for you:

Below is a Gallery of other Dresses, and Accessories I've found but not included in the above outfits. All perfect for the Kentucky Derby .