Being asked to judge a Fashions on the Field event is such an honor for me. My first international invitation was two years ago, at the Ellerslie Prix De Fashion races in Auckland. This year’s Wellington Cup was my second.

The lovely ladies, Bridget, Lucy, Jess and Caitlin from the Wellington Race Club committee invited me to come on board the judging panel for their biggest race day of the year, Wellington Cup Race Day. I didn’t have to think too hard about it. Yes please!

The Night Before Wellington Cup Race Day

I caught the early Friday morning flight and was met at the airport by the lovely, bubbly and kind Bridget. She took great care in chaperoning me around, making sure everything went smoothly and ensuring I had a fantastic time!! The volunteers at race clubs really do so much hard work and such a commendable job.

The beautiful Rydges Hotel was my home, as they sponsor the event. I found myself in a luxurious Superior King room- talk about making me feel like a VIP!

Rydges Wellington Hotel room

Image: Rydges Wellington. Rydges is central to everything, within walking distance to restaurants and cafes. The staff are all super friendly too. If you’re having a trip to Wellington, I definitely recommend staying here.

After checking in, Bridget and I had a scout around at the shops in town which allowed me to get a feel for the city. I will definitely have to make a proper trip back to do some serious sightseeing- I’ve heard just an hour away there are a bunch of wineries all within walking distance of each other with beautiful scenery too- sign me up!

While in town, we popped into the hair salon that sponsors the event as they would be doing my hair the next morning.

Buoy Salon is amazing! If you’re ever in Wellington and need some hair play, pop in here! It is on the top floor of a building with plenty of glass windows and natural light. All the workers there are so hip and trendy, rocking some seriously lush and enviable hair. No wonder they’ve won numerous hair awards and trophies. I was in good hands and looking forward to my return the next morning to have my hair styled by Michael Beel. I crept his Instagram and saw he was awarded NZ Hairdresser of the Year three times!

Bridget and I had a delicious dinner at an Asian restaurant in town, called Dragonfly. I definitely recommend it, and you must order the ‘three cheese parcels.’ My mouth is watering just thinking about them!

asian restaurant cuisine

Getting Ready for a Day of the Races

It was a relaxed start on Saturday morning, getting up at 7am to head down to the buffet breakfast- I LOVE a good buffet. Especially when I’ve got a forgiving outfit planned. I could eat as much as I wanted :D

rydges hotel buffet breakfast scrambled eggs baked beans potatoes

Tummy full I headed to Buoy Hair where Michael did me a fabulous big classic bun. I don’t have very long or thick hair so I always use padding to puff my hair out!

milano imai purple peacock millinery turban

milano imai purple peacock millinery turban with big bun rear photo

I love a big classic bun and having your hair styled on race days is a must! It helps to balance out your millinery- let’s be honest here, this piece would look a little big for my head if I had just done my hair by myself in a small bun or ponytail.

The outfit I decided on was my favourite purple, hot water bottle dress. I chose this dress because it was the only dress I owned with long sleeves, and when I packed, the weather forecast for the day was cold and windy. It actually turned out to be sunny and quite nice! I have worn this dress about five times before!!! Talk about a serial outfit repeater, but if you love it- wear it!

milano imai purple dress worn multiple times restyle rewear recycle adapt change

Just a few outings haha! I definitely got my money’s worth for this dress!

I was also dying to wear the Peacock Millinery Turban I had made by Belinda last year. It’s one of my favourite millinery pieces, so lightweight and easy to wear. I love how it looks so regal, though some racegoers said I looked like a bunny, so maybe I’ll wear it again at Easter time haha.milano imai racing fashion blogger purple dress with purple turban

The Fashions on the Field Judges and Prizes

Judging contemporary and classic categories is quite hard. I wrote a blog about it here.

When there’s a themed FOTF competition, entrants get rightfully annoyed when judges don’t stick to the theme and the rules. It’s a bit unfair. So, I always take extra care to abide by the guidelines. There’s no point having a theme if the judging isn’t going to honor it.

For contemporary and classic, there is often a lot of trouble deciding what category to put yourself in. It is also up to the judges’ interpretation of what they think classic and contemporary racewear is. Confusing.

Alongside me on the judging panel was Julia Leuchars, marketing and brand communication director and co-designer for Trelise Cooper, Stephanie Murray, Wellington Race Club Fashion Ambassador and Mathias Te Moananui, winner of L’Oreal NZ Hairdresser of the Year 2016/17. A very stylish bunch indeed!!

fashions on the field judges bio

wellington cup race day 2020

Wellington Cup has a variety of FOTF categories to enter. Firstly, there is Maiden of the Carnival, which is for ladies and gents that have never won a FOTF category before. Then there’s Classic Lady of the Carnival, Contemporary Lady of the Carnival and Gentleman of the Carnival.

fashion competition theme categories

From each category there is a 1st Place, Highly Commended (2nd Place) and Millinery winner. From the winners of each category, a Supreme Winner is then chosen to take out the grand prize. And there were some amazing prizes on offer too including shopping sprees, hotel stays and hair packages!

wellington cup fashions in the field prizes


Wellington Cup Category Winners

Maiden of the Carnival

We started with the Maiden of the Carnival Category. I love the idea of this category because it’s for ladies and gents who have never won a category before. It is a great way to encourage newbies to have a go without the pressure and intimidation of going up against more experienced competitors.

Our winner was a lovely lady whose name I didn’t catch! She wore a beautiful pink and red polka dot dress featuring a pleated skirt. She accessorised with a red boater, white bag and heels. She really nailed this outfit!

pink dress with red polka dots red boater hat fotf winner

race day photo on stage fashions


Our runner up winner wore a purple and blue floral printed dress. We especially loved the way she accessorised her outfit, even wearing two different coloured thin belts together, a clear clutch with purple insert, pink gloves and lilac strappy shoes! She did a wonderful job.

purple blue floral dress and purple wide brim hat


Our Millinery Winner made her own hat! We loved the geometric cut-outs in her hat which we later learnt was a place mat she had painted and shaped. She added some pink flowers to the underside to tie in with her pink top.

diy headpiece placemat geometric cutout pink top

maiden of the carnival millinery winner


Classic Lady of the Carnival

For our Classic winner, we couldn’t go past Gabby. We loved the silhouette of her dress, which embodied classic racewear. She wore an elegant off the shoulder turn over which finished to the side with a tie, and a midi length pencil cut skirt. She accessoried her outfit beautifully with contrasting blue accessories, including an acrylic marbled blue handheld bag, red and blue stone earrings and a textured raffia boater by Claire Hahn Millinery. Gorgeous classic attire.

classic lady of the carnival winner wellington cup

Gabby is so cute, when her number was called as the winner she was clapping away, looking around, not even realising it was her!!

red dress with blue accessories race day

I also love hearing about fun (stressful) behind the scenes stories of race ladies. Gabby said that she had a disaster start to the day with her hair and makeup lady mixing up the day of her event and not being able to do it, but she managed to find another lady to fit her in! I love a happy ending!

Our runner up was Eleanor, who wore a stunning white satin Aje dress with a yellow and black floral print. The dress was slightly risque for classic racewear, featuring an open back and sides, but the overall look and styling was very classic. I loved her Monika Neuhauser black disc hat with veiling on the underside, the silhouette looked very classic Dior.

yellow and black floral print dress classic lady category

race day style yellow and black floral print dress dior hat

I love seeing photos of Eleanor, she is always so poised and beautiful in every photo!

Our Classic Millinery winner was Claire Hahn. Everyone adored her hat! It was shaped like a rear facing beret, made in a cream vintage material, and had a big upside down green bow with a brooch. Her outfit was incredible as well, we all loved the green and pink together and her styling is always on point!

classic millinery winner claire hahn