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Now based in Tauranga with her husband and two children, Highfield says a turning point came when she celebrated her 40th birthday last year.
“I did a big speech about how in the next decade of my life, I really wanted to dedicate that to reawakening my creative pursuits,” she recalls.
“So I’m really proud of myself for keeping a promise to myself to enter again, and becoming a finalist is very, very exciting after a big gap of focusing on motherhood and career versus my creative interests.”
While she may have taken a break from WOW, during that gap she made her mark with several other ventures, from bespoke lingerie for burlesque dancers to an online baby clothing store. Most recently, she founded intimates and loungewear brand Dear Dylan, which she runs with two friends.
“That’s our little brand trying to carve out a bit of space in the fashion industry in New Zealand.”
However, making something for WOW is a whole other outlet for her creativity.
“I like working through trial and error, I like manipulating everyday materials to see how far I can take them and what I can create for them, so that process hasn’t changed,” she says.
“It was just sitting dormant, waiting for me to come back to it. Kind of like riding a bike, I think.”
Fifteen years since she last entered, Highfield says it’s clear the competition has grown and evolved.
“There’s a lot more international exposure… the process of entering and how you submit your garment and ship it and everything has become much more streamlined in that time,” Highfield says.
“But even the shows that I was in 15-plus years ago were just so incredible, and the creative team behind them just seem to outdo themselves every year.”
One difference for Highfield is that creating a WOW entry, which typically takes months of work, now requires even more of a juggle as a mum-of-two.
“It was definitely a different process this time around because when I entered 15 years ago, I was married but [had] no dependents.
“I had all the time in the world. This time, it was much different in terms of, obviously I couldn’t just tap out and go to my creative space and just do a twelve-hour stint working on it.”
This time, she fit it in amid school pickup and her kids’ dinner and bedtime routines.
“Once I had the idea and I was in the flow, it came together relatively quickly for me… the actual construction, once I can see it coming together, gets very exciting and just kind of flows.”
While the details of her 2025 entry are tightly under wraps for now, the inspiration behind it is deeply personal, reflecting her years-long battle with endometriosis.
“It got to breaking point when I was in my late 30s,” Highfield says.
She recalls experiencing “horrific pain”, 40-day periods, and days when she couldn’t face leaving the house.
“It wasn’t just something I was living with, it was really taking over my whole life and everything became about ‘When’s my period coming, how much pain am I going to be in?’”
Soon before turning 40, she underwent a hysterectomy. Although not a cure for endometriosis, it’s “helped tremendously” in relieving her symptoms.
Some complications meant it wasn’t all “smooth sailing”, Highfield adds.
“But since everything has healed and we’ve realised what medications and everything I was reacting to, I can honestly say it has been life-changing – definitely the best decision I’ve ever made.”
It showed she also had adenomyosis, a condition where endometrial tissue grows inside the muscle wall of the uterus itself.
“My gynaecologist said it’s basically endo’s evil twin, which is even more severe than the endo. [It’s] a horrific thing for anybody to go through and to live with for so long.
“I’m so glad that has all been resolved, and that part of my life was a huge inspiration in the design of my garment, which is probably a reflection of the end of that chapter.
“I really wanted to take something that has taken over so much of my life and make it beautiful and give it a finishing point. This is a representation of what I’ve been through.”
A self-confessed “crier”, Highfield is prepared to feel a wave of emotion when she sees her costume on display.
“I’ll be so proud of myself when I see the garment on stage. It’s going to be overwhelming, but I’m also like, all these incredible people have done all this amazing work.
“What a wonderful moment, and how wonderful that people can watch and experience that sort of thing and we’re able to witness it all come together – how exciting. So I probably will cry and be very emotional when I see it on stage.”
This year, her children, aged 11 and 7, will be among her supporters in the audience on the awards night.
“Obviously they’ve been through the whole process of me making it and packing it up, and they’ve got very interesting opinions on it, particularly my 7-year-old boy. He’s like, ‘Mum, that’s weird’ – which I love. I love the honesty,” Highfield laughs.
“They’ve never been to a show like that on that scale, so it’ll be interesting to see what their reaction is. I think they will be immensely proud, though.”
This year’s World of Wearable Art runs from September 18 to October 5 at TSB Arena in Wellington.
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