Artificial intelligence isn’t just the next big thing or a supercharged trend — it’s everywhere all at once.

That includes in the apocalyptic dreams of those who see an evolutionary battle between man and machine, the utopian hopes of the glass-half-full crowd and, increasingly, the strategic plans of chief executive officers.

And how could it not? McKinsey & Co. recently estimated that generative AI will add $150 billion to $275 billion to fashion’s operating profits by 2030. 

Fashion has never been the most forward-leaning of industries when it comes to the latest tech trend, but that potential is hard to ignore. 

For better or worse, AI has become almost unavoidable — and it seems set to pop up more often, in the design studio, the accounting department, the corner office and more. 

CEOs are excited and so are some workers, even if there’s plenty of anxiety to go around about what such a powerful new set of tools means for the future of their jobs and livelihoods. 

And that’s probably because, apocalyptic or not, the advent of AI is evolutionary in nature — the technology is changing fast. Brands, chief executive officers and workers are going to have to keep up and evolve as well, turning more toward what only people can do — for now at least.  

“While AI is transforming how we produce, I think it hasn’t yet proven that it can transform why we create something,” said Martha Pease, former chief marketing officer and founder of Illustra. “In an industry built on emotion and identity and taste, that’s still the most valuable kind of question in the room: Why is somebody going to be drawn to this particular aesthetic?”

“That whole aspect of applying creative judgment, whether it’s strategic judgment or production and innovation judgment or general management judgment, there’s creativity involved in all of that,” Pease said.

To understand how creativity is meeting the rising tide of technology, WWD interviewed CEOs, strategy consultants, a digital product creation expert, executive recruiters, an HR chief and the tech executives driving change through retail companies on AI. 

What emerged was a kaleidoscopic picture of a future that is defined by, yes, disruptive change, but also opportunities to take a big step forward. 

Many big names in fashion are in the glass-half-full crowd — and that might well be because the other side of the AI debate isn’t about the glass being half empty but being poured out entirely and smashed on the floor. 

Here’s what the people who think there will be a future are thinking about AI — from how to get an AI fashion job to how the new technology is changing design, connecting with consumers and more. 

The CEOs Jump In

Levi Strauss & Co. was early to start thinking about how AI would change its business and, in 2021, started to develop some internal talent with artificial intelligence and machine learning boot camps. 

The idea was for employees who went through the program to take those skills back to other parts of the business, like retail.

And the AI wheels are still turning at Levi’s. 

“We’re in the early stages here, but we’re embracing it,” said Michelle Gass, CEO of Levi’s. “Whether it’s using AI in design or using it in digital or using it in supply chain, in finance, there are different tools and capabilities that we’re exploring, that we’re experimenting with,” she said. 

That runs from taking on new challenges to trying to solve the age-old problem of sizing in fashion. 

“We’re a very size-intense business and having AI be helpful in ensuring that we have the right sizes for our fans is huge,” Gass said.  

Styling and store experience are also high on Gass’ AI list. 

“If you envision a day where you go into a store and just in one device, any question that a consumer might have, kind of like ChatGPT or Claude or Perplexity or pick your favorite, we will have that version for Levi’s,” she said.

At Vans parent VF Corp., which is already in the midst of a major transformation and turnaround, CEO Bracken Darrell is leaning on his tech background as the former chief at Logitech and getting excited about AI. 

“This can unlock more creativity, certainly more efficiency and more growth,” Darrell said. “We’re really trying to build a learning company where we’re building academies along all of our functional excellence lines, like merchandising, design, etc. An academy company is a learning machine, and we want all these people in here learning all the time.”

That learning is going to happen quickly. 

“I fully expect that people’s jobs are going to change a lot over the next year, much less five years,” he said. 

As optimistic as Darrell is, he’s mindful of just how potent this new technology is.

“I have the same long-term questions that everybody else does,” he said. “But I’m very excited for the next decade.” 

Darrell also said people have to, well, retain the ability to be mindful as the use of AI grows. 

“It’s important to keep exercising your brain,” he said. “What we don’t want to do is let a part of [your] brain go to sleep. 

“Just because you have a calculator doesn’t mean you shouldn’t learn how to do math,” he said. “We’ve got to keep doing that so that we stay facile and we can connect different ideas to each other.”

Hooray for the Humanities

The rise of the internet, e-commerce, social media and the rest of it brought a very particular skill set to the fore. The people who could code and were willing to move fast and break things were the ones with all the heat, the big jobs and big inventions. 

The tip of the AI talent pyramid is still in that mode, with the tech giants reportedly spending hundreds of millions of dollars as they staff up for the revolution. 

But lower down the org chart, potential is growing for people who don’t necessarily have the hard-core tech skills but are keen to engage with the new technology. 

Roseann Lynch, chief people officer at Ralph Lauren Corp., said: “When we look for talent, we’re continuing to look for storytellers, continuing to look for people who have intellectual curiosity and just a deep ability to probe and communicate as the purpose of the company is to inspire the dream of a better life through authenticity and timeless style. 

“We’re still looking for people who come as their authentic selves, have a story to tell about themselves, have a contribution to make in the organization that’s inspired by creative thinking and how to create an experience for people, how to humanize an experience for people,” she said.

Lynch said as she sees potential hires, she’s looking for people with degrees in the humanities or liberal arts more so than a specialty in engineering. 

“The days of these very specific skills as an area of primary focus are actually going to end,” she said. “We’re going to be thinking about people who are much more well-read.” 

Part of that is because interacting with generative AI programs is something like a never-ending game of “Jeopardy” where ChatGPT has all the answers, and you need to provide the questions. 

“AI is only going to provide you the answers to the questions you know how to ask,” Lynch said. “It’s only going to be as good as the questions you ask it. 

“In the old days, you would test a person’s capabilities based on their absolute skills and qualifications to do a job, their ability, their capacity to take in information and utilize that information to do their job well,” she said. “In today’s landscape, it’s more about knowing what questions to ask.” 

The Right Prompt

“There definitely is a skill and a craft in prompting” an AI program, said J.J. Camara, Tapestry Inc.’s senior director of digital product creation, who’s helping stitch together new processes behind the scenes at the Coach parent company.

“We’ve also identified training — training the model — as a role,” Camara said. “My team are the trainers, and then all of our designers are the prompters.” 

And Camara’s team brings a wide range of backgrounds to the effort.

“We have fashion designers, textile designers, game developers, product engineers,” she said. “We have a multimedia expert and that is part of our secret sauce. 

“No one has done this,” Camara said. “We aren’t learning this from anyone. We are learning it on our own. Often we’ll have a challenge around a project that we’re trying to execute, and the whole team will come together with their different expertise to crack the code and figure out how to develop it.” 

The technology just kind of finds its place in the work flow.

“So instead of sketching something on a cocktail napkin, [designers] are prompting it in AI and sending that quickly to me” to build out the idea digitally, she said. 

In cases like that, the AI picture isn’t perfect, but gives a sense of where the designer wants to go.

When Camara saw that, she thought, “Oh my god, I didn’t even think about them using it as a communication tool to us.”

It’s a tool that the next generation is growing up with. 

“Kids are doing AI every day,” Camara said. “They already know. Some people who aren’t early adopters of AI think that there is an issue with it, but it turns out a lot of these people early in their career, they’re using it for 10 things a day.” 

How to Get an AI Job

There’s more than enough angst to go around about what the rise of AI will do to the workforce — from the difficulties of training older workers to whether the new tech will lead to an implosion of the white collar world. 

The truism that gets thrown around a lot is that it’s not AI that’s going to take your job, but a person using AI.

Given that the big tool everybody will use in five years probably hasn’t been invented yet, how does one keen on working in fashion get an AI job? 

Tony Bacos, the Amazon fashion alum who is now chief product and technology officer at Stitch Fix Inc., advised that applicants need to “demonstrate curiosity.”

“There is no shortage of free and really deep information [on AI] available, whether it’s on YouTube or podcasts or blogs,” Bacos said. “Are you curious and are you pursuing that and scratching that itch of curiosity by reading and watching things and experimenting and getting an OpenAI or a Gemini subscription and tinkering? 

“Do you understand what these things can do even if you’re not necessarily understanding how they do it?” he said. “If we’re looking for engineers to build and train these underlying foundational models, that’s a very different skill set than looking for someone who’s a marketing specialist or a product manager who doesn’t necessarily need to know how the engine works.” 

Bacos said people need to go beyond just being able to type something into ChatGPT and understand and know how to use a “pipeline,” automating certain elements while using AI. 

“Oftentimes, you need to be able to build a pipeline that has various stages and steps that can take input beyond just a prompt that you type in. So really what it comes down to is people who have been curious enough and sort of self-starting enough to dive into that,” he said. 

While workers today with any tenure have grown used to a steady drum beat of technological change, the pace is only picking up and, unlike other much-hyped advances, it doesn’t look like this one can be ignored. 

“Remember NFTs and Web3, all those things that just weren’t a thing? This is not that,” said Lindsay Stevens, senior partner at executive search firm Kirk Palmer Associates. “This is such a thing that we can’t ignore it. And those who do will fall behind and the executives who aren’t embracing and encouraging it on the daily basis will be the businesses that fall short. 

“I feel a lot of anxiety from my clients around it because they don’t want to be left behind,” Stevens said. “It is moving so quickly that it could be tomorrow that they lift their head up and are like, ‘We didn’t do it.’ There has to be a strategy. 

“Every single person at every single level of the company needs to be using it and working together on how they actually take whatever insight or output it gives you and how you decide to apply it across the business.”

Zero Lines of Code

Even the biggest companies are pushing AI through all of their workforces. 

Dave Glick, senior vice president of enterprise business services at Walmart, is responsible for “putting AI in the hands of every [corporate] associate every day.” 

That’s a lot of hands as Walmart has a large corporate office and, overall, employs 1.6 million people in the U.S. alone.

Glick is also looking for new hires to be curious, adventurous and tenacious when it comes to using AI. 

“What we see is the people who are really great at this go and say, ‘AI, give me an answer to this.’ And it gives them an answer and they say, ‘oh, that’s not exactly what I wanted.’ And they’ll go back again and again and again. And the first time, it may take hours to get to where you need to be.” 

Everyone from associates to high-level tech types are being pushed to take that journey now.

“For the first two years of AI, the world is like, ‘Oh no, we’re scared.’ And finally six months ago, we said, ‘It’s time,’” Glick said. “I asked my most senior engineers, the technical fellows, which are folks who have 20 years of experience, ‘Go build something. I don’t even care what it is. Go solve some problem using AI.’ And they came back and said, ‘This does more than I could ever have thought it would.’ 

“This iterative process with pioneers and trailblazers, we’re out there chopping through the jungle,” he said. “They will come back and teach us lessons, but we want more. We don’t want just the technical fellows. We want everybody chopping through that forest.” 

And the path is being made quickly.

For instance, sales development representatives at Walmart were spending a lot of time making powerpoint presentations. Glick sat an engineer down with one of them for a week and they built an AI tool that allows the salesperson to get a big head start by just putting in the name of a company and letting the machine work its magic. 

“We’ll build a PowerPoint deck to sell to them and build a narrative about the company, what they sell, how to contact them,” he said. “All of these things that used to be a multi-hour process, we can now do in five minutes so we can have our people out talking to the customer.”

It’s a development process that looks very different than it would have not that long ago. 

“Our best engineers have written zero lines of code in the last six months,” Glick said.

The Economics of Using AI

That PowerPoint example from Walmart, which has been getting techier quickly, shows the potential to use the technology to save time. But it’s the second part of that equation — freeing the salesperson to be out talking to customers — that Walmart is emphasizing.  

Rebecca Homkes, a consultant and high-growth strategy specialist, said companies are going to be focusing more and more on that second part.

“If your key metrics are cost-saving and time-saving and personal productivity, you’re behind. That’s where the leading companies were three to four years ago,” Homkes said. “Now we’re looking for metrics like repurposed time. So, yes, you might’ve taken five hours out of a process, but it really doesn’t matter unless you’ve repurposed that time to more value-creating activities.” 

And retailers are going to have to put that repurposed time to work because they aren’t the only ones with AI. 

“Your consumer is going to be asking, comparing and learning about you on their AI engine of choice,” Homkes said. “Do you know how you show up there and what you need to optimize?”

Optimizing seems to be the word of the day — be it for consumers, companies or the workforce, which is in flux.

“The mainframe replaced a lot of roles, too, as did the internet, as did your mobile phone,” Homkes said. “But companies now need [to consider] who’s going to shape AI, who’s going to govern AI? We need new roles and governance. There will be new roles created just as there’s roles that are replaced. That goes back to repurposing.”

So just what are employees going to do as AI steps in? 

That might end up being the next most important question in a decade that’s already seen a pandemic, a flare-up in racial tensions, political upheaval and war.