I Let Ralph Lauren’s New AI Dress Me

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.

Here’s how the tool works: Download the app on your phone and ask it anything related to putting an outfit together, including whether you’re looking for something specific. Suggestions are tailored to what is currently in stock and available to shop, all of which aligns with your style.

Before Fashion Week, a time when even fashion editors get flustered over what to wear, I Asked Ralph what to wear.

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.

What jeans should I wear with a Fair Isle sweater?

For this look, I had something specific in mind. I knew I wanted to wear a Fair Isle sweater and jeans, but I couldn’t quite decide on which type of denim to choose. Usually, I’m quite decisive, but I wanted a second opinion, and Ask Ralph came back with these white jeans, which were just perfect. I loved these sleek boots to offset the ease of the oversize jeans and the novelty of the sweater. This oversize suede Polo Play bag was something I saw at the store and added to complete the look. (It pairs well with just about anything!)

How do I style a barn jacket with tailored pants?

I have an endless supply of barn jackets in my wardrobe at this point, but it truly seems like you can never have enough. The barn jacket I saw at the Polo store had a bit more weight to it, which felt practical and perfect for transitioning into the colder months ahead. I wondered what Ask Ralph would say about pairing it with tailored pants, because you typically think of a barn jacket as something you wear outside the city, and I wanted an outfit that I could wear to the office. Sure enough, it came back with this elevated preppy look that feels perfect for that September feeling of back-to-school (a.k.a. returning to the office): a crisp blue button-up, a corduroy vest—and all of the classic Ralph Lauren fixings for fall (a suede Polo ID bag and Western boots, of course!).