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Ad From dressing TV talent to racegoers, Sheridan Paine lives and breathes fashion. Married to jockey Regan Bayliss and a familiar face at Flemington, she knows her way around both style and the winner’s circle.

Bold, modern, unforgettable racewear with Sheridan Paine

12 August 2025 Written by Celia Purdey

Drawing on both industry experience and personal flair and an assistant stylist to Suzy Eskander, Sheridan Paine has a sharp eye for racewear that strikes the right balance between timeless and on-trend. Here, she shares what makes Melbourne’s fashion scene so distinctive, how to dress for four seasons in a day, and the little details that can take an outfit from polished to unforgettable.

Melbourne has its own unique fashion flair. What sets racewear here apart from everywhere else?

Melbourne is known for its street style and edgy fashion, and I think that spirit really comes through in racewear. People here tend to be more experimental when it comes to racing fashion, which brings a vibrant and dynamic energy to the track. You’ll always see someone pushing the boundaries – and to me, that’s exactly what fashion is all about.

How can racegoers honour tradition while avoiding being stuck in the past?

Horse racing has such a rich history, and with that comes many traditions. I believe it’s important to honour these, and that can be as simple as ensuring your outfit aligns with the dress regulations set by the club and reflects the theme of the day – for example, wearing black and/or white on Derby Day.

For women, a nod to tradition can also mean incorporating a millinery piece or hair accessory into your look. This doesn’t have to be elaborate – it could be as simple as a headband or a bow. Even within these traditions, there’s still plenty of room to have fun and bring a fresh, modern twist to your outfit.

What are some innovative ways to refresh racewear without compromising its elegance?

Accessories! They’re the perfect way to elevate any race day outfit, whether you're keeping it classic or opting for something more understated. You can completely transform your look by layering jewellery, adding a vintage brooch, or even throwing on a pair of oversized sunglasses. The possibilities are endless – they’re an easy yet impactful way to take your look from simple to standout.

Monochrome

Monochrome

Vibrant colour

Vibrant colour

Accessories

Accessories

What is your top tip for staying stylish and comfortable?

My number one tip for anyone attending the races is: wear good shoes! It’s a long day on your feet, and there’s nothing worse than dealing with blisters. Choose a pair you know you can last in all day – that goes for the guys too!

How can racegoers express their personality while still aligning with the tone of the Carnival?

Expressing your personality through your outfit during the Carnival is all about creativity and confidence. You can do this through colours, bold accessories, and interesting silhouettes to make a statement. The races are the perfect opportunity to have fun with fashion.

For example, if you love bold styles but find Derby Day’s black-and-white theme a bit limiting, you can still stand out by experimenting with patterns, textures, and layering – all within the monochrome palette. The same goes for Oaks Day: you don’t have to wear pink or a dress to look feminine. A well-tailored suit can be just as elegant and powerful. Reinterpret the dress codes in a way that feels authentic to you.

Is there a key detail or accessory that can instantly elevate an outfit?

I love how a pair of sunglasses can instantly complete an outfit. In Spring 2024, we definitely started seeing more people incorporating them into their race day looks, but I think statement sunglasses will play an even bigger role this season. Whether it’s bold frames, tinted lenses, or oversized shapes, they’re the perfect accessory to add personality and polish.

What’s one bold fashion choice you’d love to see more people embrace at Flemington this year?

 I’d love to see more people wear bold patterns and vibrant colour combinations at Flemington this year. It’s such a great way to nod to vintage trends while adding a playful vibe to the track. Mixing patterns or pairing bold hues is a great statement and brings a refreshing energy to racewear. The Spring Carnival, in particular, is all about celebrating individuality and having fun with fashion – and what better way to do that than by experimenting with colour and print.

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