What To Wear To The Races: Style, Confidence, and Cup Week Fashion
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How to Look Good and Feel Confident on Race Day
What to Wear to the Races: Style Rules That Still Matter
What to Wear to the Races in the Rain
Behind the Scenes of a Fashion Show: Judging the Best Dressed Competition
Christchurch Cup Week: A Fashion Calendar Highlight
Fashion & Racing: Key Facts and Figures
Sustainable Fashion and Outfit Recycling
What to Wear to the Races: Male Style Tips
Fashion for All: Size, Age and Self-Expression
Final Thoughts: More Than Just a Dress-Up Day
The Style for Life podcast, hosted by fashion stylist and accountability coach Stephanie Rumble, continues to be a trusted voice in New Zealand's fashion and wellness landscape. In episode 28, Stephanie welcomes Zane Tate, fashion coordinator for Riccarton Park, to explore everything you need to know about what to wear to the races — from choosing the right race day dresses to understanding race day etiquette and what judges look for in the best dressed competition. This episode is packed with insight, personality, and practical advice for anyone preparing for Christchurch Cup Week or a race event anywhere in the country.
How to Look Good and Feel Confident on Race Day
Race day isn’t just about the horses – it’s a celebration of style and self-expression. Feeling confident in what you wear begins with understanding your personal style and dressing in a way that respects the occasion. Stephanie and Zane stress the importance of authenticity, comfort, and confidence.
"It’s not about being perfect — it’s about being prepared, polished, and proud of how you show up." ~ Stephanie Rumble
When you feel great in your outfit, it shows. Whether you’re dressing for elegance or edge, the secret to how to look good and feel confident lies in thoughtful preparation and a few key style decisions. More than simply choosing the trendiest pieces, it’s about aligning your look with your own sense of self.
Here are a few tips to help boost your confidence:
Choose an outfit that reflects your personality and flatters your shape
Make sure your clothing fits properly and allows you to move comfortably
Accessorise with intention, but don’t let one piece overpower the look
Consider how you’ll be photographed or seen throughout the day
Wear what makes you feel bold, secure, and self-assured
These strategies apply to both newcomers and seasoned racegoers. Confidence stems from preparation, comfort, and believing in your own fashion choices.
If you’d like help building your confidence through what you wear, Stephanie’s personal styling service offers expert guidance tailored to your personality, lifestyle and goals.
What to Wear to the Races: Style Rules That Still Matter
Understanding fashion for the races means knowing the traditions and the unspoken rules. Raceday fashion is rooted in elegance and sophistication, with a few essential style pillars.
"Your look should be cohesive from head to toe — it should tell a story." ~ Zane Tate
Dress codes for the races may vary by venue, but some standards remain consistent. Stephanie and Zane both stress the importance of keeping your look refined and occasion-appropriate. Looking stylish doesn’t mean going over the top – it means staying true to the spirit of the event while showcasing your individuality.
Keep these foundational rules in mind:
Daytime elegance: Dress for a daytime event, not a night out
Modesty still matters: If your dress is short, go for sleeves or a higher neckline
Respect the environment: Grass-friendly heels or wedges are often a smart choice
Race day dresses should be tailored, seasonal, and event-appropriate
Adhering to these norms helps create a cohesive visual atmosphere at the races and ensures that everyone feels like part of the celebration.
What to Wear to the Races in the Rain
Weather is always a wild card in New Zealand, and the forecast doesn’t always cooperate during Cup and Show Week. Knowing what to wear to the races in the rain can help you look stylish and stay dry, without sacrificing comfort or fashion appeal.
Rather than letting the weather dampen your outfit plans, consider it an opportunity to layer with style and intention. Rainy days can be just as fashionable as sunny ones – if not more so – with the right planning.
A few wet-weather styling essentials:
Layer smart – Light trench coats or stylish capes work beautifully over formal wear
Opt for waterproof, fashionable footwear options like heeled boots
Choose hats or headwear made from water-resistant materials
Avoid delicate fabrics that water can damage easily
Carry a sleek umbrella that complements your look
"We’re not looking for perfection, we’re looking for polish and intention." ~ Zane Tate
Planning for the rain shows forethought and allows you to fully enjoy the day. Wet weather shouldn’t mean second-best fashion. In fact, a well-layered, practical outfit can stand out just as much as bold colours or prints.
Behind the Scenes of a Fashion Show: Judging the Best Dressed Competition
Stephanie shares her personal journey from competitor to judge, offering unique insights into how best dressed competition entries are judged. As part of her involvement in the racing circuit, she has judged and been involved in more than one fashion show, where creativity, coordination, and confidence shine through. According to Zane, the judging process at Riccarton Park involves attention to detail, creativity, fit, and appropriateness.
For those entering a race day competition, knowing what judges value is key. This isn’t just about wearing a pretty outfit. It’s about intention, polish, and how all the elements work together. Your clothing, shoes, accessories, and even your posture will be noticed.
Here are the key judging criteria:
A coherent and well-thought-out look
Seasonal appropriateness, especially for spring racing attire
Proper fit and tailoring
Quality accessories, especially millinery (headwear)
A confident presentation
It’s important to remember that these competitions aren’t about perfection. They’re about presentation and presence. Showcasing your own sense of style while adhering to the expected codes can help you stand out.
If you’re interested in running or improving fashion events, or want team-specific training in confidence and presentation, Stephanie also offers custom workshops and education programmes tailored for organisations.
Christchurch Cup Week: A Fashion Calendar Highlight
Christchurch Cup Week is the most anticipated fashion event on the New Zealand racing calendar. It’s not just about horse racing – it’s about community, creativity, and high fashion. The combination of Christchurch Cup Day fashion, competitions, charity events, and high-stakes racing means it's an exciting time to dress up.
"Confidence always comes across on stage. We can see if someone feels good in what they’re wearing." ~ Zane Tate
Stephanie and Zane discuss the rise of spring racing fashion and how locals are pushing style boundaries more than ever. The energy is palpable. The mix of tradition, innovation, and celebration is what sets Cup Week apart.
For those new to the scene:
Start with classic silhouettes and build in trends
Think colour, contrast, and creativity
Remember: Cup Week fashion is elevated but not costume-like
Cup Week is a place where New Zealand fashion takes centre stage. It’s an opportunity to support the New Zealand fashion industry, explore trends, and celebrate seasonal style.
Fashion & Racing: Key Facts and Figures
The impact of racing fashion in New Zealand isn’t just felt on the track – it’s supported by impressive nationwide engagement and cultural momentum. From economic contributions to community creativity, the stats tell a compelling story:
Fashion competition entries continue to climb, with over $20,000 in prize money awarded nationally in 2024 (Auckland Racing Club)
In the 2022/23 season, the New Zealand racing industry attracted more than 639,100 racegoers nationwide (LoveRacing NZ)
Many finalists in the Ned Prix de Fashion 2025 created handmade or custom garments – showcasing New Zealand’s love of originality (Auckland Racing Club)
During the jumps season, classic staples such as tailored wool coats, belted trenches, and longline blazers in navy and camel were key race day recommendations (Love Racing NZ)
Together, these numbers highlight the strength of New Zealand’s fashion-meets-racing culture, with creativity, tradition, and individuality leading the way.
Sustainable Fashion and Outfit Recycling
One of the most important themes in this episode is Stephanie’s commitment to sustainable fashion. She encourages listeners to repurpose and rewear past outfits creatively, rather than buying new for every event.
This idea aligns with the growing awareness around conscious consumerism in fashion. With a little effort, you can look fabulous without contributing to excess waste. Sustainable choices don’t compromise style – in fact, they elevate it.
Here are a few ways to dress sustainably for the races:
Mix and match separates for different looks
Rewear standout pieces with new accessories
Hire or borrow fashion for one-off events
Alter past favourites for a fresh take
By leaning into recycling, hiring, and restyling, you become a part of a fashion-forward shift that benefits both your wardrobe and the planet. It's a great way to express your creativity while staying true to ethical values.
What to Wear to the Races: Male Style Tips
When it comes to what to wear to the races for men, style is often overlooked. But men have their own standards to meet – especially if entering competitions or attending Cup Week events.
Zane breaks down the essentials for pulling off a winning men’s outfit for the races. While women may have more options, the expectations for men are just as high in terms of polish and presence. Whether competing or spectating, dressing well shows respect for the event.
Key tips for men:
A proper suit (season-appropriate in colour and fabric) is a must
Accessories matter: add a pocket square, cufflinks, or a bold tie
Well-kept shoes – no sneakers
Your men’s outfit for the races should be tailored and polished
Hats are optional but can elevate the overall style
"The races aren’t a costume party. It’s fashion, yes, but also tradition and occasion." ~ Zane Tate
A good rule of thumb: if you wouldn’t wear it to a wedding, you probably shouldn’t wear it to the races. Simple adjustments to your usual formalwear can help you achieve a memorable and stylish look.
Fashion for All: Size, Age and Self-Expression
Stephanie and Zane are clear: fashion for the races is not limited by age, size, or gender. From plus size race dresses to race day dresses for women over 50, inclusivity and self-expression take centre stage.
The podcast makes a strong case for fashion as a tool of empowerment. Regardless of your shape or age, you deserve to feel your best. Choosing the right fit and understanding your proportions makes all the difference.
This is where stylists like Stephanie truly shine, helping clients unlock the style that reflects their personality and lifestyle. Fashion should work for you, not the other way around.
Final Thoughts: More Than Just a Dress-Up Day
What to wear to the races is a question of more than just fabric and fit. It’s about embracing identity, enjoying the process of dressing up, and being part of a vibrant social and cultural tradition.
Stephanie Rumble’s podcast episode shines a light on the fun, the etiquette, and the empowerment that comes with race day attire. With expert tips from Zane Tate and decades of experience from Stephanie, listeners walk away with a guide not just to what to wear to the races, but how to show up authentically and stylishly.
Whether you're planning your first Christchurch Cup Day fashion moment or returning for another season of best dressed competitions, remember that style starts with self-awareness. Choose outfits that speak to who you are, and the confidence will follow.
For anyone looking to combine appearance with inner change, Stephanie also offers accountability coaching to support personal growth, mindset, health, and wellness.
Listen on Spotify
Frequently Asked Questions
What are the signs that someone doesn’t know how to dress well?
Some common signs include clothes that don’t fit properly, poor grooming, or outfits that don’t suit the context or body shape. For example, saggy or tight clothing, wearing items that cling or ride up, or skipping basic grooming can all signal a lack of understanding of appropriate dress standards. These signs might suggest the person hasn’t been taught about dress etiquette or doesn’t prioritise appearance.
How do you approach someone about inappropriate clothing?
Start by identifying the specific issue and refer to the company’s dress code rather than making it personal. It's important to approach the conversation with empathy and tact. Hold the conversation privately, and when possible, use the moment to educate rather than shame the individual. If you're in leadership, model the standards yourself.
Why do some people struggle with dress codes?
There can be many reasons: cultural differences, financial constraints, or simply never having learned what's appropriate. Some individuals may also view clothing as unimportant or anti-establishment. In such cases, it's helpful to approach the topic with understanding and offer practical solutions or guidance.
What should be included in a company dress policy?
A good dress code policy should be inclusive, practical, and aligned with your company values. It should set clear expectations around modesty, hygiene, footwear, and clothing types without being discriminatory. If needed, professional input from a stylist can help create a policy that balances professionalism with individual expression.
How do you deal with body odour in the workplace?
Body odour is a sensitive topic, but it can impact team dynamics. Causes may include unwashed clothing, lack of hygiene, or ineffective deodorant. Address it privately and respectfully. It can help to include hygiene guidelines in your dress policy, and in some cases, recommend specific solutions or resources.
Is it ever OK to wear casual clothes at work?
Yes, but it depends on how "casual" is defined in your workplace. Casual Fridays can work well with clear boundaries—smart jeans and clean, well-fitted tops might be acceptable, but singlets and track pants may not be. Set expectations with visual examples, and always consider whether clients will be present.
What’s the best way to give appearance-related feedback?
Give feedback in person, not over email. Be clear and constructive, using company policy to support your points. Avoid personal criticisms and instead focus on professional expectations. Reassure the individual that the conversation is intended to help—not punish—and be prepared to offer suggestions or assistance.
How can leaders build confidence in managing appearance standards?
Start with self-awareness and education. If you're in a leadership role, consider professional development in areas like communication, styling, or leadership coaching. Stephanie Rumble offers workplace education programmes that cover professional dress, presentation skills, and workplace standards.
Are there gender-specific considerations when discussing dress?
While professionalism applies to everyone, there may be unique challenges—for example, women may need advice on undergarments and sheer fabrics, while men may forget details like belts. It's important to tailor feedback appropriately while ensuring that all discussions are respectful and inclusive.
What if someone can’t afford new clothes?
Cost can be a genuine barrier. That’s why it’s helpful to understand the individual’s background before raising concerns. Solutions might include clothing allowances, company-subsidised styling help, or recommending budget-friendly options. Stephanie’s styling services can also help people get the most out of what they already have.
