Ralph Lauren is known for its classics, but the brand has always embraced change when it comes to technology. It was one of the first fashion brands to launch e-commerce 25 years ago, in partnership with Microsoft, and now it’s teaming back up with the tech giant to launch an AI tool to help you get dressed.

Unveiled on September 9, Ask Ralph, as the AI is named, provides shopping recommendations based on your needs and learns your style the more you use it. Think of it as a 2025 take on the mythical Clueless closet, but all curated through a Ralph Lauren lens. Ahead of its debut, I visited the Polo Ralph Lauren store in SoHo, New York, to get the scoop from David Lauren, the brand’s chief branding and innovation officer. “We’ve always approached our brand with an outlook of innovation in mind,” he said, explaining that even though Ralph Lauren is often thought of as a “heritage brand” with classics and wardrobe staples, it’s constantly evolving. Right now, the technology is like a sales associate who is in training and learning about the customer. In a few months, its knowledge of your likes and wants will be as though it’s worked at the brand for years.



What should I wear to Fashion Week in the fall?
I asked a general question to see what results would arise, and the Ask Ralph tool led me to this look, which I love. At first, it gave me three options for style direction, and so I went with this slipdress. Then it prompted me to ask if I wanted to look further into outerwear options, and voilà—it suggested the perfect mix of a menswear-inspired tailored jacket to pair with a sophisticated slipdress. There were additional accessories that I was drawn to from its suggestions, such as these boots, to make it feel a bit cooler. I added a belt for extra adornment to lean into the Western vibe.

When it was revealed in 2019 that Facebook was paying teens to install an app that spies on them, it was a scandal. The following year, headlines buzzed again when it was discovered that app store analytics providers operated dozens of seemingly innocuous apps to collect usage data about the mobile app ecosystem. There are regular warnings to be wary of VPN apps, which often aren’t as private as they claim. There are even government reports detailing how agencies regularly purchase personal data that’s “commercially available” on the market.

Now AI agents regularly join meetings to take notes, and always-on AI devices are on the market. But at least in those cases, everyone is consenting to a recording, Daniels tells TechCrunch.

In light of this widespread usage and sale of personal data, there are likely now those cynical enough to think that if their data is being sold anyway, they may as well profit from it.

Unfortunately, they may be sharing more information than they realize and putting others’ privacy at risk when they do.