The racing will be thrilling on Christchurch Casino NZ Trotting Cup Day but for many of those in attendance the real contest will be the trackside fashion stakes, The Crossing Fashion Starts Here Best Dressed Competition.
Hand on heart that’s probably true for us here in the Cityscape office! It’s not too late to organise your outfit and you can enter up till noon on the day. To get started on your winning style, head to The Crossing and its great range of fashion outlets from international flagship stores such as H&M, Country Road and SEED alongside top New Zealand designers Barkers, IVYBLU, Workshop and RUBY. Madisons Off Broadway offer a stunning range of special-occasion wear, with brands such as Calvin Klein, Michael Kors and Ralph Lauren. To give you the inside running, we check in with judges Deanna Didovich, designer with RUBY; Shelley Ferguson, editorial director of home and fashion magazines at Bauer Media; and head judge Jackie O’Fee, owner of Signature Style, to see what they are looking for in a winner. Heats and semi-finals of The Crossing Fashion Starts Here Best Dressed Competition will be held in The Edge Public Village To enter online and to download the judging guidelines, head to
Q&A: Shelley Ferguson
Shelley Ferguson is editorial director of home and fashion magazines at Bauer Media.
What’s the golden rule of race day fashion? Look fabulous, feel amazing, be comfortable!
What will you be looking for on the day? I’d love to see modern formal looks, defined silhouettes and some bold colour. I also love classy headwear so I’ll be looking for statement pieces that cleverly complement the rest of the look.
How important is it to work a theme? So important! Having an overall theme and approach means your entire outfit is cohesive and considered. If you shop for individual pieces you love, they may not all work together. Finding a common element from the start – whether it be a theme, colour or shape – makes it easier to shop and creates an outfit with serious wow factor.
What advice do you have for contestants? Let your lovely personalities shine through! Have fun, be positive, dial up those smiles and have a blast.
What’s the most common fashion faux pas? Too many OTT fussy details all worn together. Sequins, feathers and patterns are fun but can look overwhelming when all worn at the same time. Oh, and women in heels they can’t actually walk in! It’s a long day so comfortable shoes are a must.
What’s the best way to get the judges’ attention? Be yourself, be proud of how you look and own it. A woman’s natural confidence is the ultimate accessory to a great outfit.
How do you nail selecting a hat or fascinator? Seeing ‘Dresscode: Fascinators required’ on an event invite can be slightly terrifying! But Cup Day is the perfect occasion to experiment and a well-chosen headpiece can completely elevate an outfit. And remember, a headpiece can be a band, bow, clip, hat or fascinator, so there are plenty of practical options that don’t look like feather dusters. It can help to consider your face shape – if you have an oval-shaped face then a headpiece with more width is a great choice. Usually I choose my dress first as it’s the key part of my look, then I find a headpiece with one unifying feature, like shape. I like classic, chic and contemporary shapes and colour palettes – so nothing too detailed, garish or sparkly. Finally, think about your hairstyle – if you have a big, bold piece then a sleek chignon will work well, whereas a banded style is best with big bouncy curls. If you get confused, always think back to your personal style and what naturally ‘fits’ you.
What are you hoping not to see? People dressing too casually! Christchurch Casino NZ Trotting Cup Day is steeped in tradition so I think it’s important to respect that and make an effort to be suitably attired.
Q&A: Jackie O’Fee
Jackie O’Fee is the owner of Signature Style.
The Crossing Fashion Starts Here Best Dressed Competition is a highlight of Christchurch Casino NZ Trotting Day. To give you the inside running, we check in with head judge Jackie O’Fee, owner of Signature Style, to see what she is looking for in a winner.
What’s the golden rule of race day fashion? Just look gorgeous and have fun!
What will you be looking for on the day? Attention to detail, and that’s every detail from the top of your head to the sole of your shoe – it gets so hard to pick a winner that one year we really did eliminate one of the finalists due to her shoe being broken! I’ll also be looking to see on-trend looks – as an example, this year I’m expecting we’ll see a lot of statement sleeves, and I love colour!
How important is it to work a theme? It’s important that your overall look is cohesive, so if you are going for a Dior silhouette you need to make sure everything works with it, while if you are opting for something modern, like a jumpsuit, everything has to fit that look also.
What advice do you have for contestants? Make sure you’ve sorted every element of your outfit and then on the day, relax and be yourself. This is one of the best ‘dressing up’ things you can ever do, so you want to make sure you really enjoy it.
What’s the most common fashion faux pas? The wrong shoe or forgetting to style your hair.
What’s the best way to get the judges’ attention? Look amazing! Honestly, every year we are blown away by the incredible standard of the outfits. You truly need to look fabulous.
How do you nail selecting a hat or fascinator? Make sure you do your research – take a look at racewear winners internationally, particularly Australia as the seasons are the same, and see what is trending. Also, ask your milliner for advice – they work in this world all the time.
What are you hoping not to see? Too much flesh or cocktail wear. Race day fashion isn’t party fashion.
Q&A: Deanna Didovich
Deanna Didovich is creative director at RUBY.
What’s the golden rule of race day fashion? The bolder the better!
What will you be looking for on the day? I’ll be looking out for someone whose personality shines through the outfit they have put together. I am sure there will be some beautiful fashion on display, but for me it will be all about not just putting on the trendiest dress but considered styling, unique accessories and a great colour palette.
How important is it to work a theme? Anything goes! A theme isn’t necessarily important; you should work to what you feel most confident in.
What advice do you have for contestants? Don’t worry about what anyone else is wearing! Just have fun.
What’s the most common fashion faux pas? Wearing something you don’t feel comfortable in – you want to enjoy the day and feel your best.
What’s the best way to get the judges’ attention? Confidence is key.
How do you nail selecting a hat or fascinator? You can definitely be more creative in this area, using hair accessories as another option. We have a range of hair clips and headbands that could be the perfect finishing touch to a look – whether this is pairing the RUBY Dionne Headband with your outfit, or the RUBY Prince Clips with a sleek ponytail.