In Her Stride: Caitlin O’Sullivan Doyle on Raceday Style That Endures

Ladies’ Day and the sold-out Lindauer Ladies’ Lunch at Pukekohe is fast approaching – and who better to discuss the fashion, flair, and timeless traditions of the races than one of our very own ambassadors and judge of tomorrow’s Lindauer Style Stakes, Caitlin O’Sullivan Doyle?

Carrying on the legacy of her mother, Bridgette O’Sullivan – our inaugural ambassador in the early 2000s – Caitlin brings a modern yet respectful nod to the long-standing style associated with the sport.

Sharing her insights into raceday dressing and her love for the magic of racing fashion, Caitlin has some top tips for creating the perfect raceday ensemble.

Club ambassador, Caitlin, pictured here at our 2024/25 Season Launch event

What initially inspired your interest in fashion and raceday dressing?
I love the tradition that goes hand-in-hand with racing, and I think dressing up is such a fun part of that. Raceday is the perfect excuse to wear something you wouldn’t usually wear and celebrate the occasion in style.

As an ambassador for Auckland Thoroughbred Racing, how do you think fashion contributes to the overall raceday experience?
Fashion adds to the fun and glamour of the day – it’s all part of the magic. And let’s be honest, you can’t tell me you don’t feel amazing when you’re wearing an outfit you absolutely love!

Caitlin pictured here with her mother and former club ambassador, Bridgette (left), and sister Georgia (right) on course at Ellerslie for Barfoot & Thompson Champions Day 2025

What are the key elements that distinguish a raceday outfit from everyday formal wear?
Racing is typically a daytime event, so that’s something to keep in mind when choosing your look. While I love a modern twist, I think it’s great to nod to tradition. Headwear, for example, remains a signature element of racewear that sets it apart from your usual formal outfit.

What are your go-to tips for turning an outfit into something raceday-ready?
It’s all about the finishing touches, whether that’s headwear or accessories. It doesn’t have to be over the top, but the right details will elevate your look to ‘raceday ready’.

Caitlin was giving hair goals at last year’s Lindauer Ladies’ Lunch

Hats and fascinators are iconic elements of raceday fashion. What advice do you have for selecting the perfect headpiece?
There’s that old saying about not putting the cart before the horse… same goes for not buying the hat before the dress! Your headwear should complement your overall look. There are some incredibly talented milliners here in New Zealand (and abroad), and working with one to create something custom can really pull everything together beautifully.

How do you go about selecting the rest of the accessories without overwhelming the look?
Great question! My personal style is definitely ‘less is more,’ so I usually keep things fairly minimal. That said, I always admire those who rock a statement accessory with confidence. The key is making sure every element of your outfit works together to create a cohesive look. Each piece should add something, not just be there for the sake of it.

How do you balance style and comfort, especially considering it can be a full day at the races?
Is it bad to admit I probably forfeit comfort for style? Haha! My biggest tip is to make sure you can commit to your shoes for the whole day. There’s nothing worse than regretting them halfway through!

We found it hard NOT to obsess over Caitlin’s look on Melbourne Cup Day at Ellerslie earlier this season

What are some common mistakes people make when putting together a race day outfit, and how can they avoid them?
Perhaps trying a little hard to follow trends or what they think is ‘raceday appropriate.’ The most important thing is to wear something you love. Confidence takes an outfit a really long way.

For those new to attending racedays, what are your top three tips for dressing confidently and stylishly?
Scroll for some inspiration (Ellerslie’s Instagram is a great place to start!), choose something you genuinely love, wear it with confidence.

What is your favourite raceday outfit you’ve worn? What made it special?
My favourite outfits often seem to be linked to how the horses I’m supporting perform – this game is full of superstition after all! I’ve noticed that I tend to gravitate toward pink on racedays, so maybe my 2024 Karaka Millions outfit or my Melbourne Cup look would top the list.

Caitlin (left) with sister Georgia at the TAB Karaka Millions at Ellerslie earlier this year

Entry into the Lindauer Style Stakes at Pukekohe Park’s Ladies’ Day (25 June 2025) is free for attendees of the day’s Lindauer Ladies’ Lunch. 

Thanks to Lindauer, Racing Her Way empowered by TAB and Belinda Green Millinery, we have some wonderful prizes up for grabs for the contestants named as Winner, Runner-Up and Maiden (someone who has never won a racewear competition before).

Caitlin (check her out on Insta here) will be joined on the day’s judging panel by Wilhelmina Shrimpton and Soraya Gurney.

• Learn more about the Lindauer Style Stakes here.

Last year’s Lindauer Style Stakes winners (centre) flanked by judges Sasha Boyens (left) and Caitlin (right).