What I Wore: Kentucky Oaks

12th May, 2023

As one of the most iconic racing events in the world, I was so excited to be at Churchill Downs as a guest of the Kentucky Derby. I was thrilled to be attending Kentucky Oaks and also judging the Longines Fashion Contest. Kentucky Oaks was founded in 1875 and is the premier racing event for fillies in the US and takes place the day before the Kentucky Derby every year. Being able to attend such a historical event was such a fun experience, particularly as I was invited to judge the best looks of the day. Everyone really put forward their sartorial best with such a great array of outfits and headwear. I was also happy to see a few Aussie brands like Zimmermann and Aje amongst the sea of well-dressed ladies.

The dress code entailed incorporating pink into your outfit in an effort to drive awareness to the fight against breast cancer and ovarian cancer. I wanted to honour this while also embracing an Australian designer so I immediately gravitated towards this midi dress by Rachel Gilbert as the ideal option. It’s a quintessentially classic look and it also features a touch of pink in the floral motif. The beaded floral detail not only adds a feminine touch to the dress, it adds a beautiful flourish of colour which allows the crispness of the white to really pop.

Being on the petite side, I’m all for a pair of sky high heels so this pair by stylist Lana Wilkinson was a no-brainer. I liked the fact it continued the white colour palette, while the slimline profile and tie-up straps made for an elegant pairing with the dress. I considered a few different options in terms of the bag I was going to carry, but I eventually settled on the Jimmy Choo Micro Cloud clutch which features a delicate, oversized bow which I thought added a playful touch to this outfit. Headwear is of course a must for any racing event, and this fuchsia pillbox hat added a fun pop of colour while also honouring the dress code. Sometimes a little simplicity and elegance (and a touch of pink!) is all you really need for an outfit to make an impact.

Credits: Dress, Rachel Gilbert; Hat, Nerida Winter; Shoes, Lana Wilkinson; Bag, Jimmy Choo

This post was produced in collaboration with the Kentucky Derby


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