What to Wear for Oaks and Derby Day This Year

It’s beginning to feel a lot like Derby season in Louisville.

Hats and fascinators hit store shelves in early March and will only be making more and more appearances until the Run for the Roses on the second Saturday in May.

Louisville locals know Derby is more than just a day; it’s a week long party. Women and men prepare their outfits weeks or even months in advance. It’s essentially the biggest fashion show of the year, even for the horses. 

In case you haven’t thought about an outfit yet, I want to show you a few great options that were kindly lent to me from Six Sisters Boutique in Nulu. They’ve got a great selection of dresses, rompers, skirts, fascinators, and all other accessories you need to complete the perfect Oaks or Derby look.

(And for the record, this is probably the most color you’ll ever see me in on the blog.)


What to Wear to the Kentucky Oaks

Oaks Day is a day for the ladies, both human and horse. The Oaks race is for three-year-old fillies and attendees are encouraged to wear pink in support of breast and ovarian cancer awareness. Not that you need to wear pink to feel like a woman. Oaks Day is traditionally just as fancy as Derby day (dependent on where you’re seated), so break out your best dress/jumpsuit and hat combination.

As you can tell, I did not opt for a traditional pink outfit in this look, but rather these coral high waisted pants and white top. This outfit can easily carry you from the track to the after party and everywhere in-between. You could also repurpose this look for a number of spring or summer events the rest of the season.

I fell in love with this big white floral fascinator from local handmade designer Darling Handmades. She makes the most unique floral inspired fascinator designs for those who want something outside of the norm. You can find her pieces on Etsy and local boutiques around town like Six Sisters.

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Fascinator: Darling Handmades // Top: Six Sisters Boutique // Pants: Six Sisters Boutique // Shoes: Target 

What to Wear to the Kentucky Derby

Derby day is the day everyone dresses to the nines. Derby is a historical day with deep-rooted traditions that most people take very seriously. So when you’re planning out your week in outfits, save the best for last. Most women will be wearing their biggest and best hats, cocktail dresses, and heels, with a mint julep in hand of course. But if that’s not your thing, try a jumpsuit and fascinator.

This is another gorgeous fascinator from Darling Handmades. I immediately fell in love with how unique this fascinator was compared to everything else I had seen. It’s just as much of a showstopper as the horses on the track. The stems of it bring out the green of this shift dress, which, by the way, is so comfortable. Run to get this dress if you don’t have one for Derby already.

Pro tip: wear comfortable shoes to the track. Unless you’ve got a seat, you’ll be on your feet all day. Leave the big heels or sandals that give you blisters at home.

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Fascinator: Darling Handmades // Necklace: Missoma // Dress: Six Sisters Boutique // Shoes: Target 

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