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New Zealand Trotting Cup: Flair and individuality shine in the fashion stakes

Carefully considering the details, right down to the buttons and threads, is what made Cup Day’s most fashion-forward man a cut above the rest.

Christchurch man Matt Anderson, the winner of Addington Racecourse’s Best Dressed Man award at Tuesday’s New Zealand Trotting Cup, said his cobalt blue double-breasted suit jacket, made by Sergio’s Menswear, was entirely custom-designed to catch the eyes of the judges in front of a packed out crowd at the Lindauer Lawn.

Anderson, a familiar face in the racing fashion scene and a regular winner of best dressed events, said avoiding “boring” choices was what snatched him the win from a strong field of entrants, with most in the crowd sporting bright and colourful prints, fine millinery and detailed touches.

“I get this idea in my head and run with it .


You’ve got to do something a little bit different,” he said.

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After selecting the design for the jacket, he picked the buttons and stitching colour, and paired the jacket with crisp white pants, a floral brooch and a printed tie.

The ensemble garnered the attention of the judges: television personality Shelley Ferguson, Jackie O’Fee from Signature Style, and New Zealand-based brand RUBY creative director Deanna Didovich.

Ferguson said the level of talent in this year’s fashion pool was “unbelievable”, noting the attention to detail of the winners.


Best Dressed Lady went to Sydney-based fashion lover Nikki Pagen, who was astonished when her red and white dress was awarded the blue sash.

Hearing the squeals of delight from Pagen’s cheering friends was the icing on cake for the fashionista, who “never dreamed” she would win after seeing the strong pool of entrants.

Friends watching on from the front row whooped and celebrated as she was handed her Best Dressed certificate – an award not totally unfamiliar to her.

“I’ve won a few best dressed events before but this competition was next level .


there was such a high standard.”

She said being aware of the spring racing season’s top trends, showing individuality and flair, and “a bit of confidence” were the key elements to success, but anyone could win on the day.

Her dress, by quirky London fashion brand Ted Baker and purchased from Myer in Australia, had frilly red sleeves added to it and was paired with a matching clutch. Her hat was made especially for the occasion by a friend who recently opened a millinery business in Australia.

“She’ll be over the moon [that I won] ..

. I sent her a quick message.

Pagen’s prize includes return flights to Tokyo, a diamond necklace and matching earrings, and shopping vouchers to The Crossing.


Runner-up went to Stephanie Murray in her fit and flare bright yellow dress, along with an equally bold headpiece.


Ashleigh Tawhara, Stacey Roe and Elsa Varayeva thought their co-ordinated blazer and short looks put them in good stead for the day. Each woman complemented their outfits with enormous hats and bold accessories.

Roe said the outfits, designed by their mutual friend Sophia Lee from Living Doll, were similar, but each matched their individual personalities and put a modern twist on classic looks. Tawhara’s vintage Chanel monochromatic jacket was paired with red accessories and oversized pearl earrings, whereas Roe opted for a sky blue buttoned jacket with clear-strapped heels.

“With hats, bigger is better at the moment. I think it’s all about going big with hats, they make such a statement,” Roe said.


Some let their dresses do the talking, bringing spring florals and bright colours to the catwalk.

Although it was “always a risk” buying racewear from a well-known designer, Gabrielle Cashmore thought taking a punt paid off.

She paired her orange dress by Australian designer Mossman with cobalt blue accessories and a hat by designer Claire Hahn.

Buying a dress off the rack meant she risked losing out in the fashion stakes if another entrant wore the same item but “thankfully that didn’t happen”.

“I’ve heard it can basically mean you lose your spot because it shows you aren’t original and I totally understand that but that didn’t happen this time”, she said.

Waiting for garments to arrive pre-race day was the most stressful part, often involving obsessively tracking her parcel across the country to her front door, she said.



Style-forward Cantabrian Michael Stanton said by opting to wear a bespoke black headpiece to Cup Day on Tuesday, he was careful the high fashion nod not be taken as a “gimmick”, pairing it with an Art Deco-inspired look and custom suit.

Stanton approached Christchurch-based hat making company Seventh  Figg and couture milliner Susi Meares more than a year ago to discuss ideas, and had his first fitting in April.

He wanted to show the traditionally conservative crowd at Addington Raceway that it was possible to look masculine and strong while wearing a headpiece, a goal he is confident he achieved despite not taking home the prestigious Best Dressed Man title. 

“I wanted to make a point of difference .


I’m young at heart.”

Stanton said he was strongly influenced by Art Deco style for his black and brown suit and tie combo, which was not dissimilar to the architecture, block colours and designs that surrounded him during his time living in the French Concession in Shanghai.

Stanton returned to Christchurch in 2013 and said as the city grew, a growing number of creative people were filling its streets. 

“There’s a new tone to the city, we’re a very creative bunch of people.

Meares was in charge of the structural design of the headpiece, opting for simple lines and six black quills to imitate a cage. 

“We’re really pushing the boundaries here, things like this can put Christchurch fashion on the map,” Stanton said.

Once the headpiece design was secure, Stanton‘s personal tailor made a custom suit from Italian linen to complete the look.

He is not a stranger to fashion.

In 2017 he took out the title of Best Dressed Man at the Fashion in the Field comparison at Riccarton Park Racecourse in 2017, which was his first year competing.

Being knocked out this year was “very disappointing”, but celebrating the day at Louis Champagne Bar in the afternoon took the edge off.

“The feedback was exceptional, really amazing. I feel like we’ve really been shining a light on what can be done.


Cup Day’s popular body art contest had been a long-running part of the event, but was quietly dropped from this year’s programme. 

Previous competitors were told the event was not going ahead several months ago by email.

Yoobee School of Design Christchurch head of makeup department Angela Pethig, who has body painted for 28 years and twice won the Cup Day competition, said organisers were unable to tell her why it was not running. 

She said she understood there had been a change of sponsors, and the event would be considered again next year.