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50 Best Kentucky Derby Dresses 2023 | Chic Womens Outfits

50 Best Kentucky Derby Dresses 2023 | Chic Womens Outfits

kentucky derby dress what wear womens outfit

What to Wear to the Kentucky Derby – Show up in style! The most elegant Kentucky Derby attire for your most stylish horse racing outfit yet

Kentucky Derby dresses and outfits for women 2023 mean finding something fabulous, elegant and something a little more statement making than most of our everyday attire. From stunning hats and fascinators to the most fashionable dresses and jumpsuits. I’ve always loved dressing up for the horse races. Whether that’s Royal Ascot, Newmarket or the Goodwood Races. It’s one of those times, besides weddings, where you can wear a really fabulous hat. Whether you’re looking for a classic chic style or something more on trend, these are the most beautiful dresses for the Kentucky Derby and Kentucky Oaks (it’s Sister event) that I came across. As well as some fashion tips for finding the perfect Derby dress. 

This Kentucky Derby outfits for women post contains affiliate links.

best kentucky derby womens outfit dress blazer set

When and where is the Kentucky Derby 2023

The Kentucky Derby 2023 is on May 6th at Churchill Downs. With over 150,000 attendees gathering under the Twin Spires at Churchill Downs to watch the 14 horse races.

Things to consider when choosing your Kentucky Derby dress

You’re going to want to take into account the dress code in the enclosure or reserved seating areas you’re in and the weather when choosing your Kentucky Derby dress and outfit. Some areas require more formal dress codes than others. Their full dress code requirement for each enclosure is here.

kentucky derby dress one shoulder blue midi

While there is no dress code for guests purchasing reserved box or general admission tickets to Churchill Downs, management reserves the right to deny admission to anyone whose attire they consider to be inappropriate.

Churchill Downs

How to dress in layers for all weather at the Kentucky Derby

Your best bet is to dress in layers for Kentucky Derby week. The Kentucky Derby is an outdoor event and you want to be prepared come rain or shine. Blazers, capes, trench coats and elegant pashminas are all ideal for layering over Spring dresses and lighter fabrics.

I also really like matching blazer and dress sets for being able to layer easily. Whether that’s bold separates or pretty pastels. They’re perfect both on cool Spring days and hot days in the Summer. As often the AC is too cold or the temperature drops at night.

Feathers and satin don’t fare too well in the rain unfortunately. So you might want to take that into consideration when choosing or designing your hat, shoes and Kentucky Derby dress.

If you’re not going to Churchill Downs but to a Kentucky Derby themed party, especially one that’s inside you can have more fun with your shoe and hat choices. As you don’t have to worry about the weather so much.

What shoes should I wear to the Kentucky Derby

Most people will tell you to wear sensible shoes and something that you can walk on grass and gravel in. Which is the best advice. However, rules were made to be broken and most if the time I’ve just worn a pair of strappy, stiletto sandals to the races as it makes the whole outfit look so much more elegant. As long as you can still walk in them! 

Just remember it is a long day to be on your feet so if you don’t go for sensible heels, you might want to pack a pair of back up flats. Or even better fold-up flats you can keep in your bag if you need them.

what heels wear horse races
White heels sold out | Similar square heels

This year I went for a square heel to be able to walk on the grass and they were absolutely perfect for walking around in.

dress horse races floral midi
I find this style runs big, you may wish to size down.

Should I choose my hat or Kentucky Derby outfit first

It really comes down to personal preference on whether you choose your hat or Kentucky Derby dress first. If you fall in love with something get it.

If it’s the hat you that you find first there are so many choices on line that you can filter by color to find something that will work. If it’s the dress you fall in love with first, you can always work with a milliner if you can’t find the perfect hat.

If you’re going for a really elaborate Kentucky Derby hat, a plain dress might be a better bet so that you can let your hat be the focal point. However, if your hat is more simple or 1 color, a pretty floral print dress often looks really stunning.

kentucky derby dress 2023 pink midi elegant
Photo Revolve

What are the best Kentucky Derby dresses for 2023

The best Kentucky Derby dresses for 2023 are the ones that speak to you the most and that you feel confident in. The perfect dress for one person, is different to the next persons.

Personally I like bright colors, pastels, floral prints or fresh polka dots for the horse races and avoid darker colors. Did you know that it’s actually considered unlucky to wear black to the derby! If my hats got a lot going on, I tend to always go for a more plain dress rather than prints and always one that coordinates for chic Kentucky Derby fashion and a more polished look.

You can also look to Vineyard Vines for dresses. As the official style of the Kentucky Derby, they have created a line of dresses just for the Kentucky Derby. However, their 2023 collection hasn’t been released yet and I tend to prefer to plan ahead.

Some of this years biggest color trends are pastels, magenta, sunset colors, aquamarine, green and metallics. Just be careful with wearing metallics during the day that it doesn’t get too glam. Think more elegant garden party than disco diva for Derby day.

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leather shorts womens fashion blogger Glamour Gains brunch outfit

Complete your womens Kentucky Derby outfit with the perfect shoes and bag

This is the time to have fun and go all out with your fashion and fancy hat choices. Just be careful with your spacial awareness and your hat around other people!

Since pink is a big color trend this year, there’s lots of pink hat, shoes and accessories in various shades on this edit. Please take note of the bag size restrictions before making a purchase (more details below).

If you’re wanting to go all out with your Derby horse racing hat, have a look at Jenny Pfanenstiel designs. She was named the featured Milliner for the 146th, 147th, 148th and 149th Kentucky Derby and offers both ready to wear and custom designs.

What am I wearing for the 2023 Kentucky Derby Party in Vegas? That’s a surprise but I’ll update this post with photos from the event for some ideas for next years outfit.

What size bags are permitted at Kentucky Derby week

The Churchill Downs Racetrack enforces a restricted bag policy for Kentucky Derby week. From Saturday April 29th, 2023 through Derby Day on Saturday, May 6th, 2023 each guest is only permitted one bag no larger than 12″ x 6″ x 12″. 

Where to party in Vegas for the Kentucky Derby

If you want to celebrate and help a local charity, check out the Answer 4 Cancer Kentucky Derby Gala on April 21st 2023. My beautiful friend Misti is the founder and you can learn more about the charity organization here.

answer 4 cancer kentucky derby gala


Don’t forget to tag me in your Derby day outfits #glamourandgains @glamourandgains so that I can share your fabulous Derby style (s). Cheers, I’ll be the one with a mint julep in hand in a giant hat.

Good luck!

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