I Tasked Ralph Lauren's AI Stylist With Outfitting Me for Fall—See How It Did

For years, the Ralph Lauren brand has been synonymous with a particular styling sensibility, one that's tailored, classic, a bit preppy, and always inimitable. Of course, producing the same results while putting together outfits at home is never as seamless, which is why the brand is launching Ask Ralph. A digital styling and shopping tool powered by AI that's exclusive to the Ralph Lauren app, it's programmed to solve all manner of styling woes and shopping pursuits—anything from what to wear to the office to sourcing the perfect thing to gift someone, and so much more.

For every query, the app produces three outfit options and from there you can narrow it further and further until you land on your perfect look. Over time, the idea is that it will get to know you and your style preferences and be able to make suggestions that are hyper-personal. "It should be a fun learning tool," says David Lauren, the brand's Chief Branding and Innovation Officer. To Lauren, you the beauty is "learning about fashion history, style, and how to put things together that you maybe wouldn't have otherwise though to." It's like having a pocket stylisy at all times to share cool ideas and translate the brand's sensibilities for whomever, wherever, from a shopper in New York to a client in China. "You get to ask 'What would Ralph do?'" Lauren says.

I spent an afternoon tinkering with the AI stylist and had it product three fall outfits for me. For each of them, it took my no more than one or two follow up questions to land on a look I was ready to pull for my dressing room. From a fall wedding guest look to an elevated way to wear the iconic Polo baseball cap, see which outfits it picked out for me and shop them each here.

Look 1

The Prompt: "What should I wear to a fall wedding?"

The Look: With wedding season in full swing, putting together a look to wear to attend fall nuptials was top of mind, so the first thing I asked the style assistant to do was put together some outfit options. Naturally, it pulled a selection of the pretty midi and maxi-length dresses from the brand's seasonal offering, each with accessories like shoes and bags to match.

One of the first suggestions was a satin bias-cut slip dress that could easily be worn to a wedding and then repeated for cocktail events and dinners thereafter—understated and versatile. I found that having the app complete my outfit with the right finishings took the guessing game out of things and one part that I appreciated most. It married the navy slip with camel-hued accessories: a pair of strappy sandals and Ralph Lauren's sleek Polo ID Clutch Bag.

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Look 2

The Prompt: "How should I style a Polo baseball cap for fall?"

The Look: I arrived at the brand's SoHo boutique just as the US Open was coming to an end. I had seen plenty of celebrity and fashion-person looks styling the iconic Polo baseball cap for the occasion and knew I wanted to add one to my own closet. I plugged "How should I style a Polo baseball cap for fall?" into the search bar and was promptly met with a range of outfits that leaned into the hat's sporty vibe, but determined to arrive at a more elevated look, I refined my search results further until I landed on something more polished: a striped button-down shirt, a pair of curved tapered jeans and Polo's newest denim silhouette, and classic penny loafers. To tie it together with that signature Ralph Lauren styling, the AI called for the addition of a mini ID bag in brown suede and thick cable-knit socks to layer underneath the denim.

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Look 3

The Prompt: "Show me a casual-cool way to wear a barn jacket."

The Look: Lastly, I narrowed in on one fall trend that Ralph Lauren is doing especially well right now: the barn jacket. From my initial search, I found the exact style I wanted to build my outfit around, the Cotton Utility Jacket, and then redid the search to get outfits that revolved only around that style. The brand's signature preppy aesthetic was among the first round of styling suggestions, so I used keywords that were truer to my personal style like minimalist, sleek, and trend-forward to land on a look I knew I'd feel excited to try on IRL. The result was a base of the same Curved Tapered denim with a heavyweight white T-shirt and Western ankle boots to give the jacket a bit of edge. I was immediately a fan.

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