Heathermary Jackson is cool. Objectively so. The Kiwi-born, New York-based stylist has just finished a long day of planning potential looks for upcoming shoots when we sit down to chat via video call. She’s particularly looking forward to the one she’s doing with model Abbey Lee Kershaw and legendary photographer Cass Bird (whom she has collaborated with countless times). Over the next couple of weeks, she’ll also be styling models Precious Lee and Emily Ratajkowski respectively.

Shoots such as these are just another day in the proverbial office for Jackson, whose portfolio reads like the credits of an ensemble cast film. You’d be hard-pressed to find a magazine she hasn’t shot for or a celebrity she hasn’t worked with. After speaking with her for only a few minutes, it’s obvious that her tenacious spirit (and no small amount of talent) have helped get her where she is today.

The youngest of seven children, Jackson was adopted and raised in West Auckland by a pair of school teachers, and spent much of her adolescence invested in music, dance, and drama. “My mum wanted any of us to be interested in dance and musical theatre and performing,” she explains, “and then I came along and I was into it.” It was Jackson’s biggest dream to attend the prestigious Juilliard performing arts school in New York City, and at the tender age of 16, she wrote the institution a letter and managed to wrangle herself an interview. “Looking back, I’m like, ‘that was pretty cool that I managed to do that’,” she says. “I didn’t go, couldn’t get visas or anything, but it was a dream that I had.”

While performing took up a large amount of her free time growing up, Jackson admits she’s
always had some level of interest in fashion. “I was really into clothes. I would change outfits all the time, much to my mother’s annoyance... there would be piles of clothes on the floor and I wouldn’t clean them up.” Juilliard may not have been an option, but the creative always knew she was destined for bigger things, and, rather than worrying about academics, she set her sights on moving overseas. “My focus was on the performing stuff and saving money to get out of New Zealand,” she says candidly.

At 20, Jackson moved to England where she attended the London Academy of Performing Arts and, while working part-time at a restaurant to pay her way, she was introduced to someone who landed her an internship at fashion PR agency Club 21. At the time, the agency represented labels such as DKNY and Bvlgari, and one of Jackson’s first-ever projects was managing the celebrity guest list for a major fashion party. “I’ve always said that I fell into it,” she says of her journey into the industry. “I met people that I liked and took the opportunity to work for free for three months at [Club 21] and learned a lot.” The rest, in a way, is history — after a short while of working there, she realised that the fashion industry was where she wanted to be.

After spending a couple of years assisting other stylists, Jackson ventured out on her own, becoming a contributor for titles such as Dazed & Confused, i-D, and The Face, while also working with various musicians. “I did a lot with the band All Saints and the last two Spice Girls videos... worked a lot with Richard Ashcroft when he left The Verve, so kind of a lot of music in the beginning,” she recalls.

Gaining recognition for her impeccable eye and pioneering of the high/low fashion trend, Jackson soon found herself sitting at the helm of The Face as fashion director — a role that led her to work with celebrities and high-profile photographers, including Steven Klein and Terry Richardson. Of all the shoots she styled during her tenure there, the November 2002 cover with Macaulay Culkin stands out as a particular highlight. “When I get someone who’s down — Macaulay Culkin was totally down — when you get someone who’s really into having fun and creating something, then it’s really cool,” she says.

In 2001, Jackson made the permanent move to New York shortly after 9/11. Having now been based there for nearly 23 years, she’s been an editor for titles such as Teen Vogue and America magazine, styled some major campaigns and runway shows (including several for Karen Walker) and had contracts with Sephora, Steve Madden, Victoria’s Secret, and Vans — to name a few. Despite having all these major achievements under her belt, Jackson struggles to answer when asked to identify the moment she felt like she’d ‘made it’. “I look back at the early 2000s here and in London, and then just my career — you know I worked for 10 years with Steven Klein and did some incredible shoots,” she says, “It was blood, sweat, and tears. I look back on those days and I think they might be the highlight.” Currently, Jackson is the fashion director-at-large for Puss Puss magazine, which has seen her work with many iconic cat lovers including Grace Coddington and Jamie Bochert.

Though working in the fashion industry has obvious privileges, between the cost of health insurance and tense political climate, working in America is not without its challenges. During the peak of the Covid pandemic, Jackson and her daughter Chloe spent eight months living in Aotearoa, and while she contemplated staying for longer, the creative felt it wasn’t the right time for her workwise. However, with the next presidential election looming, Jackson admits that she’s been considering the move more seriously. “Tempers are high, it’s stressful here,” she says. Given that her own daughter is transgender, the idea of Trump’s Project 2025 coming to fruition is particularly distressing.

But it’s not all bad. In 2012, Jackson launched Brownstone Cowboys, a vintage website that she decided to turn into a magazine during the pandemic. Through the platform, she has been able to give back in her own way, covering topics that are close to her heart, including politics, sustainability, and social issues — her most recent project a vintage auction to fundraise for abortion access. “That’s one thing I really enjoy doing: something creative around something that’s really important,” she says. “It doesn’t make me any money; it’s a passion project.”

The fashion industry is often accused of being shallow, so it’s heartening to hear how Jackson is actively making a difference. Whether or not she decides to return to Aotearoa, she’s not only inspiring us with her visionary styling, she’s making the world a better place for us all.

Words: Amberley Colby. 

Images: supplied.

This feature was published in the spring 2024 issue of Fashion Quarterly.