what to wear to the races – thoughts from the kentucky derby

16th May 2023
Thoughts from the Kentucky Derby...

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Having been to Cheltenham and Ascot here in the UK, I thought I knew what I was signing myself up to when I attended the Kentucky Derby last week – the most attended and highly anticipated horserace in America held at the legendary racetrack, ‘Churchill Downs’ in Louisville, Kentucky. 

My goodness me was I wrong though!

From the hospitality and genuine friendliness of everyone we met to the incredible fashion on display (when I say that America knows how to dress the part, I mean it!) it was in a completely different league to any sporting event I’ve experienced. I’ve never seen so many Oscar De La Renta dresses in one place. And Ali and I have been left with memories that will last a lifetime because Kentucky certainly knows how to put on a show. 

Which is why I felt inspired to do a run down of my fashion choices throughout the weekend…

Should you find yourself wanting to go next year – I highly recommend it – or are seeking some outfit inspiration for Britain’s upcoming races.

For Kentucky Oaks Day

Held on the day before Derby Day, Kentucky Oaks is modelled on the British Epsom Oaks race and all guests are encouraged to wear pink to support the Surivors Parade that takes place before the race – a march of breast and ovarian cancer survivors that has raised more than $1 million so far. With that in mind, I opted for this Treillage-print cotton bustier dress from Giambattista Valli and accessorised it with my blush pink Lady Dior and the most elegant rose coloured headband and bow from Emily London headwear. To say that the craftsmanship of Emily London is impeccable would be an understatement. I felt so elegant all day and went on to win at the races too! 

For The Barnstable Brown Gala

Conde Nast recognised The Barnstable Brown Gala as one of the top ten parties in the nation so I knew that I had to raise my game for this one! Held on the eve of Derby Day, previous guests include Kim Kardashian, Tom Brady and the legendary Paris Hilton. It’s hosted at the organisers’ house (two twin sisters who have dedicated their lives to philanthropy) and the night has raised over $17 million for diabetes charities since it first launched. Though we were so jet lagged on the night, I felt so lucky to be there because Boyz II Men performed live and I got to rewear my beautiful blue gingham gown from Luciana Amelia that I purchased last year. Paired with my Christian Louboutin heels and Dior bag, it’s one of those statement dresses that instantly transforms your mood. And given that it was black tie, I found myself feeling so inspired by so many other dresses on display throughout the night.

For Derby Day

Apparently the Kentucky Derby’s association with fashion was established by Meriwether Lewis Clark Jr (the Founder of the Kentucky Derby) who envisioned the Derby as a high-class event like European-style racing events. If you ask me though, the fashion at Kentucky shows us Brits up! More so than ever on Derby Day itself – the two minute race that millions of fans in over 118 countries tune into worldwide. 

I opted to wear an old Erdem dress with this wide brimmed ‘Provence’ hat from Emily London – a piece that I’ve had on my wish list for ages so finally got an excuse to buy it! I’m certain that hospitality is in American’s DNA because I’ve never received so many compliments wearing an outfit in real life before. It’s also worth noting that I’ve had this Erdem dress for four years now. It never fails to make me feel good when I wear it – A telltale sign of a good investment purchase if you ask me!

So there you have it! A whirlwind of a weekend that I am so grateful I got to experience.

A huge thank you to Churchill Downs for hosting us – I can’t wait to return one day soon!

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