When Gladys Lai described her role as Head of Brand at Vogue Australia as that of a “custodian”, my mind went to The Lord of the Rings.

There is a scene in The Lord of the Rings: The Fellowship of the Ring, where Gandalf stands alone on the Bridge of Khazad-dûm, suspended above a dark abyss, as the rest of the Fellowship races through the Mines of Moria. As the Balrog descends upon them, Gandalf raises his staff and declares, “You shall not pass.”

While Lai’s remit is less apocalyptic, the comparison is not such a far cry. 

As Head of Brand, she is responsible for safeguarding the voice of Vogue Australia: deciding what belongs within its world, what must go, and what shall not pass. And yet, she is not simply guarding the bridge. 

She is building one of her own, framing fashion through the lens of history, politics and aesthetic theory, and bringing her distinctive way of seeing to an institution she has been entrusted to preserve.

I sat down with Lai to discuss the craft behind her editorial voice, the making of a career in fashion media, and what it takes to preserve the authority of a legacy title in an era of collapsing attention spans.

On Writing as Her First Love

Long before Lai entered fashion media, she was a devoted reader. 

By the age of nine, she had already fallen in love with Jane Austen, Virginia Woolf and Tolkien. Writing grew alongside that appetite for literature. 

“Writing was my first love,” she tells me, “and I think it really has underpinned everything that I have come to love in the years since.”

When I ask who her style icons were growing up, Lai tells me she was drawn less to celebrities than to imagined worlds: the medieval armour, elaborate headdresses and costumes of The Lord of the Rings, Disney princesses, ancient Egyptian jewellery and the clothing preserved in art and history.

“I feel like all of those style influences were drawn from areas that weren’t strictly, conventionally fashion,” she says. “It was clothing in the sense of a study of how people used to dress and what it says about a culture and a time.”

That instinct still shapes her work. Lai does not treat fashion as an isolated subject, but as a way of reading culture, history, politics and aesthetics.

On Studying Law 

When I ask whether she had always imagined a career in fashion media, Lai laughs and shakes her head.

“I never considered it as a career path,” she says. “I don’t think it was painted out as possible for me. No one I knew worked in fashion.”

Her understanding of the industry was, by her own admission, limited to The Devil Wears Prada. The life she pictured for herself was quieter.

“I wanted to work in a library or an archive somewhere,” she confesses, “somewhere decidedly maybe unfashionable and a bit naff.”

When I ask why she initially pursued law, Lai is clear that it was never the dream. Neither, at first, was journalism. She had planned to study arts and pursue history or art history, but conversations about prestige, employability and the apparent waste of good marks pushed her towards a combined law degree.

“I had conversations with people about the so-called prestige of studying a law degree alongside an arts degree, and how I would be, quote unquote, ‘wasting the marks that I got’ if I just did an arts degree,” she says.

She is less diplomatic about that logic now.

“That is obviously such a backwards way of thinking. It is not how anything works, and it is really regressive.”

The promise attached to law was familiar: stability, professional legitimacy and a career path visible from the outside. Lai describes it as the “safety net” she had been told she needed, although the metaphor looks less convincing in retrospect.

“At the stage of my life where I am now, I think it is very funny that a safety net is a five-year degree in which you need to do another year of practice before you get admitted,” she says.

She remains grateful for the degree. Law taught her resilience, though her interest lay in the parts of the curriculum that rewarded argument, interpretation and the written word.

“It was the historian in me that found the most interest in the least fiscally attractive parts of a law degree,” she says. “I loved writing essays.”

Throughout her degree, writing remained the constant.

“I had considered writing secondary to all of these other things and all of my other interests,” she says. “Then I thought, what if just the craft of writing was the job?”

On Her First Day at Vogue 

Lai’s entry into Vogue came when she was about 19, midway through her degree, after the kind of chance encounter that sounds as though it belongs in a film. She met the then editor-in-chief at a networking event; they spoke, and Lai was asked to send through her résumé. An interview followed soon after.

For the occasion, she wore a black woollen turtleneck, gingham cigarette trousers and a pair of little black Repettos she still owns.

“It was very Audrey Hepburn, Roman Holiday kind of style,” she says. “Very straightforward. I was not trying to do anything. It was just a little bit more put together.”

The romance of the beginning soon gave way to discipline. Lai interned for a year while studying full-time and working two other jobs. Some days began at seven in the morning and ended with lectures or tutorials late in the evening. Her weekends belonged to her second job.

“I would literally never do that again,” she says. “I don’t know why I did that to myself.”

The internship itself was unusual. On her first day, rather than being relegated to coffee runs, Lai was asked to review a Louis Vuitton Cruise show. She had never written about a runway before.

“Completely fresh,” she says. “I just launched into it. I had no clue what I was doing. I just started writing.”

The piece was published, and more assignments followed.

“I was writing from day one,” she says.

Years of reading had already given her an instinct for structure, even if the subject was new.

“I think I understood what structure was demanded of me by the task,” she says. “It came pretty naturally.”

On Becoming Head of Brand

Lai did not arrive at the Head of Brand role through one swift promotion. She noticed what was missing, then began doing it.

“I have, and still do have, a tendency to overexert myself and overextend myself into other parts of the job,” she says. “If I see a gap in a workflow, I will just fill it.”

As a content editor, that meant taking on work that sat beyond the formal limits of her title. 

“I naturally took on all of these other responsibilities that no one else was claiming,” she says. “I was like, ‘Well, I would like to have my title reflect that difference.’”

Her interest was never limited to the page. The writing mattered most, but so did the machinery around it: where money came from, how editorial decisions were made, how an audience behaved and how commercial interests shaped the work.

“The purely creative part of the writing is always going to be what drives me,” she says. “But I was also interested in how the business ran, where money came from, how money influenced what we wrote, and just having a more 360-degree picture of the business.”

That curiosity led her into strategy, data and analytics, then into a Head of Brand role at GQ and later Vogue Australia.

“It is a very widely spread-out role,” she says.

Writing, interviewing and editing remain central. Lai fields pitches, helps writers shape and structure stories, and decides whether an idea belongs within the editorial world of Vogue. The role also extends into social strategy, audience development, community building, video production and commercial partnerships.

“I have a very clear understanding of what is off brand, and how to make something that is off brand on brand, or whether it should not be a Vogue topic,” she says. 

Custodianship, in this sense, involves knowing the institution intimately enough to recognise its boundaries and knowing when those boundaries should move.

On How to Write for Vogue

Fashion media has a reputation for opacity, and Lai does little to dispute it. 

“It is not very clear how to get into it,” she nods. 

Her advice is simpler: reach out.

She answers DMs, meets aspiring writers for coffee and encourages people to cold email, cold message, and be “a bit annoying”. “If one person responds, it is great.”

The path into publishing is also less dependent on being chosen by a magazine than it once was. Substack and social platforms allow writers to build a body of work on their own terms. Still, Lai says the modern editor must be more than a writer. “I do not think anyone is a straight writer anymore,” she says.

A colleague recently used the term “creative generalist”, which Lai thinks captures the shift. A writer should understand narrative, but also visual direction, video, audience, packaging, commerce and platform behaviour.

“All of that is important,” she says, “and it bolsters your writing.”

On the Future of Fashion Media

The most difficult part of Lai’s role is not celebrity, pressure or the demand to produce at speed. It is the instability of the industry around her.

“Traditional media has never been in a more volatile position,” she says. 

For years, digital publishing was seen as the answer to the decline of print. That certainty has disappeared.

“People were talking about the death of print for ages,” Lai says. “Now it is even really the death of digital media.”

The line between old and new media has narrowed, while advertising money has shifted towards platforms and individual creators. Vogue must participate in that system without becoming indistinguishable from it.

“The most difficult part of the job is: how do you evolve a brand while keeping true to its roots, but also understanding that technology and consumer behaviour are shifting radically in a really short period of time?”

That question returns to the idea of custodianship. Preserving authority does not mean insisting that the future must resemble the past. It means recognising what must remain intact when everything around it changes.

Ultimately, Lai’s role places her at that threshold: between the magazine and the platform, the archive and the feed, the past and the future.

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Behind the Seams is a series by Chloe Lei that explores the paths of those who began in law before finding their way into fashion.

Through conversations with fashion founders, designers and creatives, the series offers a glimpse into what it really takes to step away from the conventional path and follow the pull of fashion.

The post A Million Girls Would Kill for This Job: In Conversation with Vogue Australia’s Head of Brand, Gladys Lai appeared first on Fashion Law Journal.

On paper, law and fashion seem to belong in two different worlds. Law is built on hierarchy, precision and precedent. Fashion is built on desire, excitement and taste. But each, in its own way, is a closed world with its own language, gatekeepers and unspoken rules. 

For Hoang, fashion did not present itself as a clear career path. “Until you are in it, unless you have access to it, or your family knows someone, or your parents know someone, it does not feel like a traditional career path,” she tells me. “It is quite opaque to people who are not already in it.”

I caught up with Hoang to discuss the law degree before the label, the making of ANNA QUAN, and the discipline behind a brand that appears effortless.

On Studying Law

You studied law and journalism before moving into fashion. What initially drew you to law?

I kind of fell into it. It was a good base to learn about the world. If you want to be a writer, understanding how the world is structured is helpful. That was something else I was interested in. I thought law would be exciting because you would meet new people and do different things.

Was there a point where you realised that if you wanted to pursue fashion instead of law, you had to do it then, rather than later?

My husband was the one who said, “If you really want to pursue this, you have to do it now, because the money is going to get too good if you do not. You will go into the job, the money will become too good, and you will never come back and do the thing you want to do.”

Did your legal background shape the way you approached building the brand?

Building the brand was more about articulating and building out product and a brand feeling. I do not think that came from studying law or becoming a solicitor. It came more from life experience. I knew I wanted to create a brand that filled a gap for me and made me feel creatively fulfilled.

On Breaking into Fashion

How did you begin to research how to get into fashion?

I was in the third year of my law degree, and I thought to myself, “I really want to do this”. I was not sure what I would do once I finished law, but I knew I had always been drawn to fashion. 

I started applying for fashion internships while I was in law school, but people would say, “No, you are not right. You do not have the training.” Then someone who very kindly rejected me said, “You should go and do this course. This is the course you study if this is what you want to do.” 

That started the process. It was research 101: what is the course, what are the requirements, how do you get in, how many people do they accept, what other courses are available, and how do they compare?

How did you get into the fashion design course?

You could not just enrol. You had to be selected. The process involved a portfolio submission, a drawing exam, a design exam and an interview. The first threshold was the portfolio. If they liked the portfolio, you were selected to sit the exam. 

The exam had two parts. One was drawing, where you had to sketch what you saw. The second was to design a winter look and a summer look. Everyone was given the same fabrics to look at and touch, and then you had to go back and sketch a winter look and a summer look. 

After that, you did the interview. They would decide how you had performed in the other assessments, talk to you, and decide whether they thought you had potential.

How did you feel going through that process?

Firstly, I could not draw. Before I could even properly consider applying, I did drawing classes for a whole year. There were thousands of people applying for fewer than 100 places. At the time, it was very competitive to get in. It was not like going to a private fashion college where you pay money and get a diploma. It was selective. You could not pay your way in. 

It was more competitive than law school.

They needed to identify that you were a member of their tribe. Fashion can be very tribal. It is not a meritocracy. Marks mean nothing. Having a high ATAR means nothing. 

You could have a great portfolio, a great drawing, and a great design on paper, but if they did not think you were part of their tribe, you were not going to get in.

What do you mean when you say, “fashion can be very tribal”?

I think you had to know and get to know the right people, and understand who would be assessing you. For me, I had already been studying with one of the teachers who was one of the core decision-makers. He had seen a lot of my drawings over the year because he had been training me for the exam.

On leaving stability behind

What did it feel like stepping away from the more conventional legal career path?

When I was studying design, towards the end of it, a lot of my friends were becoming senior associates. One of them became a partner very young, at a top-tier firm. A lot of my friends became senior associates while I was still completing my studies.

How did that feel at the time?

I wish I could say I did not care, but I did feel a bit left behind. I was still a student, and I did not really have a career path. I knew I was going to finish, but I did not know whether I would have a successful career by the end of it, or even a stable one.

Some people said I was wasting my time. They thought it was a pipe dream and that I was wasting my talent. They probably do not remember saying that now.

Was there a turning point when you felt like you had ‘made it’?

I do not think so. People might think that because I go to Paris four times a year, and to New York, London and other places, and I do lots of different things. But I never really feel like, “I have finally made it.” There is always something else you want to do or explore.

On Building ANNA QUAN

When you first launched your label, what did you need to put in place from a business or legal perspective?

We incorporated a company and registered business names and things like that. My husband is a lawyer, so I made him do it. He purchased a shelf company, registered the company. His background is intellectual property, so trade marks, names and corporate structures were things he was already practising in at the time.

When I started my own label, it was separate from the brand I initially started with my business partner. I bought back her one share in the company, and then I changed the corporate name and the trading name. That was it.

What do you enjoy about running the business side of things?

The running of the business is interesting because you get to do lots of different things all the time. There is the creative part, and there is also a lot of putting out fires. You are doing something different every day, which is very stimulating. Maybe too stimulating sometimes, but it suits me.

What does a day in your life look like?

Today, for example, I had a meeting with my team about change management and AI implementation. This morning I did filming, walking people through the new collection and creating short-form content for organic and paid channels.

There was some graphic design work, then I had a three-hour design meeting on a resort collection. I am also looking at fabric swatches, designing silhouettes, sketching, merchandising, and dealing with wholesale issues, like what to do if shipments are delayed or what we are willing and able to provide within certain timelines.

On the future of ANNA QUAN

What is next for ANNA QUAN?

For now, I am looking at consolidation. There are changes around taxes, tariffs, logistics, and the way fashion operates with the advancement of technology. The other day, we received our first agentic sale, which we were not expecting. We now have people shopping agentically for clothing. So for us, it is about consolidating a lot of social, structural and technological change before trying to scale further.

Behind the Seams is a series by Chloe Lei that explores the paths of those who began in law before finding their way into fashion.

Through conversations with fashion founders, designers and creatives, the series offers a glimpse into what it really takes to step away from the conventional path and follow the pull of fashion.

The post Before the Label: Anna Hoang on the Making of ANNA QUAN appeared first on Fashion Law Journal.

She wore it like it didn’t matter.

A narrow strip of tortoiseshell, perched on top of a crown of blonde hair.

A simple Charles Wahba headband, purchased quietly from C.O. Bigelow in Manhattan’s Greenwich Village, which opened as a true apothecary in 1838.

Now, decades later, there are lines outside C.O. Bigelow again.

Thanks to Ryan Murphy’s ‘Love Story: John F. Kennedy Jr. and Carolyn Bessette’, flocks of women are queuing up outside C.O. Bigelow to buy the headband in an effort to “get the CBK look.”

But the truth is, they can’t.

Because what made the headband iconic was not the object itself, but what it carried with it – an association with a specific woman, in a specific time in 90s New York.

Nineties minimalism was not so much a trend, so much as a way of moving through the world. In every photograph the paparazzi managed to steal of Carolyn – whether she was walking her dog, doing cartwheels at the Kennedy compound, or stepping into a gala in one of her Yohji Yamamoto dresses – there was a kind of authenticity that could not be manufactured.

She looked real. Lived in. And her clothes felt like an extension of a life already in motion, rather than something assembled for the masses.

The irony of modern style culture is that, for all its talk about individuality, it is built on replication.

“Steal her look.” “Build her wardrobe.” “How to dress like Carolyn.”

There is now an entire ecosystem dedicated to Carolyn Bessette – curated Pinterest boards and Instagram accounts cataloguing every coat, every skirt, every pair of sunglasses she wore, as though proximity to the object might offer proximity to the woman herself.

What these tributes often pay little regard to is the girl behind the clothes.

Who was the girl behind the tortoiseshell headband?

Carolyn Bessette grew up in sleepy suburban Connecticut, the daughter of a public school teacher. She studied education at Boston University.

Her entry into fashion was nothing out of the ordinary. She started on the shop floor at Calvin Klein in Boston. It was on the shop floor that she began to develop the sense of style that she would later be known for.

She moved into public relations, eventually climbing the ranks to become a senior publicist at Calvin Klein in the 1990s, at a time when the United States had entered into an economic recession and the bold, shoulder-padded excess of the 80s suddenly felt too loud.

Calvin Klein was quietly setting the visual language of modern minimalism. As Lisa Marsh, author of The House of Klein: Fashion, Controversy, and a Business Obsession, says, “Calvin Klein’s era of minimalism was a sign of the times. History remembers this era as one that is an antidote to ’80s maximalism. No one will ever don a simple slip dress without, consciously or unconsciously, saying a little thank you to Calvin Klein.”

In that context, the headband made sense. Simple, yet practical.

Now, search for “tortoiseshell headband” online, and thousands of results appear. But what is being traded is not the headband itself. It is the association with Carolyn’s style.

Which begs the question: how far does the law go in protecting personal style, and more importantly, taste?

Where the law draws the line: why personal style resists ownership

In the eyes of the law, a tortoiseshell headband is unremarkable.

A tortoiseshell headband sits almost entirely outside the boundaries of intellectual property law protection in Australia.

It is unlikely to attract meaningful copyright protection. Copyright law in Australia protects original works of expression, not ideas, not style, and not functional objects as such.

For protection to arise, there must be an original artistic work that reflects independent intellectual effort. A tortoiseshell headband, as a mass-produced, functional accessory, does not readily meet that description. There is no identifiable artistic expression in the object itself that copyright is designed to protect.

It is neither new nor distinctive, and therefore unlikely to satisfy the threshold for registrability under the Designs Act 2003 (Cth) (Designs Act).

Under the Designs Act, a design must be “new and distinctive” to be registrable. A design is distinctive if it is not substantially similar in overall impression to any prior design (the “prior art base”), as judged through the eyes of the informed user. An “informed user” sits between a casual consumer and a design expert.

Viewed through that lens, a tortoiseshell headband is unlikely to meet the threshold. The form is already well established: a slim, curved band, worn pushed back from the face, typically in acetate or plastic. These features dominate the overall impression and have existed in the prior art base for decades. Any variations in tone, finish or thickness are minor and do not meaningfully alter that impression.

And so, dupes circulate freely. Near-identical versions are produced across price points, from fast fashion to boutique labels.

The question, then, shifts to the consumer. What protects them from ordering what they think is a piece of fashion history and instead receiving a plastic torture device?

Under the Australian Consumer Law (ACL), a seller must not engage in conduct that is misleading or deceptive, or likely to be misleading or deceptive. Nor can they make false or misleading representations as to origin, endorsement or authenticity.

The prohibition applies even if there was no intention to mislead or deceive. A seller cannot suggest that a product is the same item worn by Carolyn Bessette-Kennedy, nor imply any form of affiliation that does not exist.

A seller may trade on aesthetic resemblance, but not on false provenance. It may say “in the style of”, but not “as worn by”. But it cannot assert a history it cannot prove. It can invite comparison, so long as it stops short of making a claim it cannot substantiate.

So why then do we still want to buy it?

While Carolyn Bessette-Kennedy’s headband was never distinctive in design, it was distinctive in context.

And so, you can purchase the headband, wear the black turtleneck sweater and don the mid-calf Prada boots.

But, despite the insistence of fashion magazines and TikTok creators, you cannot “steal her look”.

What you cannot acquire is the thing that made it so coveted in the first place: her taste.

Taste, in this sense, remains entirely unprotected. And entirely out of reach.

Screenshot That is a series by Chloe Mo that explores iconic fashion pieces from film, television and cultural history that live rent-freee in your mind long after the scene ends, and unpacks each item’s cultural significance and the legal issues that sit behind it.

The post On Carolyn Bessette-Kennedy & Identity: The Girl Behind the Tortoiseshell Headband appeared first on Fashion Law Journal.