What's Happening
  • Events,
  • Fashion,
  • News
    • October 24, 2025

    The Crossing Cup Day Fashion Competition Returns

    Event Essentials

    • Date: Tuesday, 11th November 2025
    • Location: The Crossing Fashion Marquee, Public Village, Addington Raceway
    • Presentation Time: 11am – 12pm (judging)
    • Winners Announced: 2:30pm (after Race 6)
    • Categories: Best Dressed, Best Suited, IRT Something Blue
    • Entry: Pre-register online or register on the day
    • Requirements: IRT New Zealand Trotting Cup Day ticket (from $25), must be 18+ and NZ resident, T&Cs apply

    Your Moment in the Spotlight

    Picture this: November sun glinting off champagne flutes, the thunder of hooves echoing across Addington Raceway, and you – dressed in your most considered ensemble – stepping into a marquee where Canterbury’s fashion future is being decided. This is your invitation to something rather special.

    The Crossing Cup Day Fashion Competition is back for 2025, and we’re searching for those who understand that getting dressed is an art form, not an afterthought. This isn’t about following trends blindly or drowning in designer labels. It’s about that electric moment when everything – the cut of your jacket, the tilt of your hat, the precise shade of your pocket square – comes together to tell your story.

    On the 11th of November, three distinct categories will unfold at the IRT New Zealand Trotting Cup Day. Whether you favour the polish of a perfectly tailored suit, the creative freedom of contemporary race-day elegance, or want to play with the sponsor’s signature hue in the IRT Something Blue category, there’s a stage waiting for your interpretation.

    The judging panel reads like a masterclass in style authority. Nik Rush brings 26 years of global design vision from Rodd & Gunn‘s world stage. Lara Olsen, who knows every thread and texture at Juliette Hogan, has spent a decade helping clients discover their most confident selves. And Gemma Kirk? Last year’s winner turned judge, she’s walked international runways and graced magazine spreads, yet remains devoted to elevating New Zealand’s fashion narrative.

    These judges aren’t looking for costume or caricature. They’re seeking cohesiveness—that ineffable quality when grooming, accessories, fabric quality, and personal confidence converge into something memorable. Your deportment matters as much as your hemline. The story behind your statement piece carries weight. Every detail, from the sheen of your shoes to the thoughtfulness of your millinery choice, becomes part of the conversation.

    Registration is open now online, though you’re welcome to enter on the day itself. Between 11am and midday, you’ll present your look to the judges in The Crossing Fashion Marquee, located within the Public Village—a space open to all ticket holders, whether you’re there to compete or simply celebrate with mates who’ve taken the plunge. By 2:30pm, after Race 6, winners will be announced from the presentation area.

    The rewards? Think seven nights on Mooloolaba’s peninsula, gift cards from The Crossing’s finest stores, travel vouchers, and those little luxuries that make victory taste even sweeter. But beyond the tangible prizes lies something more valuable: recognition from those who genuinely understand what it means to dress with intention.

    This is your opportunity to show Canterbury – and perhaps yourself – what happens when creativity meets craftsmanship, when personal style refuses to apologise, when you step into that marquee and own every second of it. The only requirement is an IRT New Zealand Trotting Cup Day ticket and the courage to let your carefully curated outfit speak volumes.

    So what will your ensemble say on November 11th? The stage, the judges, and your moment are waiting. Register now, because the best fashion stories are the ones we decide to write ourselves.

     

    Frequently Asked Questions

    • How do I enter the competition? Pre-register online through the Addington Raceway website here, or register on the day at The Crossing Fashion Marquee. You’ll need to purchase an IRT New Zealand Trotting Cup Day ticket and present yourself to the judges between 11am and 12pm on 11th November.
    • What are the three categories?
      • Best Dressed celebrates elegantly curated outfits with millinery and accessories inspired by contemporary fashion trends. Learn more here.
      • Best Suited recognises the art of tailoring—think suits or blazers with exceptional accessories and grooming. Learn more here.
      • IRT Something Blue honours our major sponsor by welcoming anyone wearing blue, from a subtle accessory to a full ensemble. Learn more here.
    • Can I enter multiple categories? You can enter either Best Dressed OR Best Suited (not both), but you may also enter IRT Something Blue alongside one of the other categories.
    • What are the prizes? Best Dressed and Best Suited winners each receive seven nights at The Peninsular Beachfront Resort in Mooloolaba, a $1,000 travel voucher, a $500 Crossing Gift Card, plus vouchers from premium brands, champagne, and flowers. IRT Something Blue winners receive accommodation in Queenstown, car rental, champagne, and a beautiful bouquet.
    • What will the judges be looking for? All categories are judged on exceptional accessory use, quality of materials, meticulous grooming, deportment, cohesiveness of the entire look, and creativity. Best Dressed and Best Suited have specific criteria, while IRT Something Blue focuses on statement blue pieces that complement race-wear elegance.
    • Who can enter? Entrants must be at least 18 years old and New Zealand residents living in New Zealand during the competition period.
    • Can I wear designer labels or promote brands? While you’re welcome to wear any brands you choose, you cannot commercially promote a brand, store, or designer, nor receive compensation from third parties for participating.
    • Can I adjust my outfit after entering? Once you’ve entered the competition, you’re not permitted to alter or add to your outfit in any way.
    • Where is The Crossing Fashion Marquee? The marquee is located in the Public Village at Addington Raceway. It’s open to all ticket holders—whether you have hospitality packages, Infield tickets, or Public Village access—so your supporters can watch and celebrate with you.
    • When will winners be announced? Winners will be revealed at 2:30pm from the presentation area, following Race 6.