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One of the biggest Southern fashion events of the year is upon us, and it calls for a fabulous frock, an eye-catching hat and shoes that you can stand in all day! The Kentucky Derby has been going strong since 1875 and with that comes a dress-to-impress attitude.

This iconic event at Churchill Downs in Louisville, KY has been on my personal bucket list for as long as I can remember. This year my wish has come true, and I’ll be attending both the Kentucky Oaks and the Kentucky Derby. And the best part is, I’ll be bringing you the fashionable scoop straight from Churchill Downs! Make sure to follow along on both my Instagram and StyleBlueprint’s Instagram to check out the best-dressed attendees, a behind-the-scenes look at the races and my top fashion picks around Louisville.

Derby fashion

How fantastic is this broad-brimmed hat made with horsehair and complete with a lush, petaled flower with glass bead centers and ostrich plumes? Image: CAM Hats

Kentucky Derby Fashion Fascinator

This trendy color offers the perfect pop of color to your Derby outfit. Image: CAM Hats

RELATED: Your Ultimate Style Guide to Derby 2019

Over the years I’ve had the pleasure of dressing numerous clients for this special weekend in May, and with that, I’ve learned the dos and don’ts of what to wear to Derby. This, of course, has helped me in planning my own ensembles for the weekend, and I hope it will help you too!

Whether you are attending the festivities in Louisville, or perhaps a Derby soiree in your hometown, you don’t have to buy an entirely new outfit to look fabulous and Derby-ready. When I am working with my style-coaching clients, I love showing them how to shop their own closets without having to hit the stores. It allows them to rework items they already have hanging in their closet for a fresh look without spending a dime. Or, if they do need an item or two to finalize their outfit, they have a game plan. They know exactly what they need and can avoid any shopping mistakes.

Kentucky Derby Fashion Fascinator

This “Sassy Statement Fascinator” is adorable and won’t break the bank. Image: Mod Cloth

The first rule in shopping your own closet for an event like the Derby is understanding the dress code, the weather, the location and your personal requirements. Establishing your personal requirements simply means being real with yourself regarding what you feel most comfortable wearing — but without sacrificing style, of course. Do you need supportive shoes with a block heel due to foot issues or the fact that you’ll be standing in the grass? Do you always get cold and need to have light layers handy? Putting in some initial legwork to assess your personal preferences and desires will save you time and money, and it will eliminate any stress as your event gets closer. Once you know these general wardrobe requirements, it’s time to shop your closet!

RELATED: ‘Lucky Kentucky’ FINDS to Welcome Derby Season: April 2019

What to Wear to Kentucky Oaks

For the Kentucky Oaks, a race for fillies held the Friday before Derby each year, it’s custom to wear pink in support of the Pink Out breast cancer survivor parade. Dive into your closet and see what frilly, feminine pink items are hiding in there. Don’t have a full-blown pink dress? No worries, try a pink top with a neutral skirt, or even a neutral dress with a dash of pink in a scarf, shoe or hat. Get creative and think outside of the box to dress on-theme without having to rush out and buy a bunch of pink items you may never wear again.

(For some pink inspiration, check out the 2018 Kentucky Oaks Fashion Contest.)

Kentucky Derby Fashion Fascinator

This floral dress features pink hues throughout, making it perfect for Oaks. Image: Dillard’s

Kentucky Derby Fashion Fascinator

The profile hat comes in three different colors and is the perfect topper for this fresh and flowy ensemble. Pink flowers pop on this pattern, making it acceptable for Oaks too! Image: Dillard’s

What to Wear to Kentucky Derby

Now on to the main event, the Kentucky Derby!

When I’ve helped my clients create a Derby-worthy outfit, we’ve always started with the hat. First, think about whether you prefer a true hat or a fascinator. If you don’t have a fun hat or fascinator tucked away in your closet, visit your local department store. Many department stores have a lovely spring hat selection this time of year as the Derby is so close to Easter, Mother’s Day and other festive occasions. If you prefer online shopping, try out consignment shops like Tradesy, The Real Real or even eBay. You can find fabulous hats for a reasonable price on these types of sites or even your local vintage shop.

Kentucky Derby Fashion Fascinator

A classic straw hat with a marigold satin bow | Image: Eugenia Kim

Kentucky Derby Fashion Fascinator

Red straw sunhat with an ivory-and-black striped band | Image: Eugenia Kim

Once the hat is finalized, bring it into your closet to see which dresses in your wardrobe might pair nicely with your hat. There’s no need to match the colors exactly, but do try to keep a cohesive look. The best way to do that is to think about the overall vibe of your look. Is it more classic and traditional? Colorful and whimsical? To achieve a cohesive outfit, make sure your dress works with the style of your selected hat.

Finally, finish off your Derby outfit with a pair of heels that you can stand in all day (or for your entire event) and some jewelry that does not compete with your hat. Et voila! You are ready for the Kentucky Derby!

Kentucky Derby Fashion Shoes

This strappy metallic heel is an airy and breathable option for a day at the tracks. Image: Anthropologie

Kentucky Derby Fashion Shoes

This blush pink heel is perfect for Oaks. Image: Anthropologie

I look forward to sharing with you all of my fashionable finds straight from Churchill Downs! Remember to follow along on StyleBlueprint’s Instagram as well as mine!


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