I Tried Ralph Lauren's AI Stylist—Three Autumn Outfits It Selected for Me
For many years, the Ralph Lauren brand has represented a specific styling aesthetic—tailored, classic, slightly preppy, and truly unique. However, achieving that same effect when assembling outfits at home can be challenging, which is why the brand is introducing Ask Ralph. This AI-driven digital styling and shopping feature, exclusive to the Ralph Lauren app, is designed to address a variety of styling dilemmas and shopping needs—from outfits for the office to finding the ideal gift. For each inquiry, the app generates three outfit suggestions, allowing users to refine their choices until they discover their ideal look. Ultimately, it aims to understand users and their style preferences, offering hyper-personalized recommendations. "It should be a fun learning tool," states David Lauren, the brand's chief branding and innovation officer. He believes it provides insight into fashion history, style, and creative combinations that users might not have otherwise considered. It’s like having a personal stylist on hand to share fresh ideas, catering to everyone, from a shopper in New York to a client in China. "You get to ask, What would Ralph do?" Lauren adds.
I spent an afternoon experimenting with the AI stylist, asking it to create three fall outfits for me. Each time, it took just one or two follow-up questions to arrive at a look I was excited to try on for myself, ranging from an outfit for a fall wedding to a chic way to style the iconic Polo baseball cap. Check out the outfits it selected for me and shop them here.
Look 1
(Image credit: Polo Ralph Lauren)
The Query: "What should I wear to a fall wedding?"
The Outfit: As wedding season is in full swing, I first requested outfit ideas for attending fall weddings. The style assistant provided options featuring gorgeous midi- and maxi-length dresses from the brand’s seasonal collection, complete with matching shoes and bags. One standout option was a satin bias-cut slip dress, perfect for weddings and versatile enough for future cocktail events and dinners—simple yet elegant. I appreciated how the app completed my outfit with complementary accessories, eliminating any guesswork. It paired the navy slip dress with camel-toned accents, including strappy sandals and Ralph Lauren's sleek Polo ID Clutch Bag.
Shop the Look
- Polo Ralph Lauren Satin Midi Slip Dress
- Polo Ralph Lauren Leather Kitten Heel Sandal
- Polo Ralph Lauren Polo ID Leather Clutch Bag
Look 2
(Image credit: Polo Ralph Lauren)
The Query: "How should I style a Polo baseball cap for fall?"
The Outfit: I visited the brand’s SoHo boutique just as the US Open was concluding. Having seen numerous celebrities and fashion influencers don the iconic Polo baseball cap for the event, I knew I wanted one for my wardrobe. I entered "How should I style a Polo baseball cap for fall?" into the app, and was quickly presented with a variety of sporty outfit ideas. Seeking something more polished, I refined my search until I found a look that resonated with me: a striped button-down shirt, a pair of Curved Tapered Jeans (the latest denim silhouette from Polo), and classic penny loafers. To enhance the look with that signature Ralph Lauren flair, the AI stylist suggested a mini ID bag in brown suede and thick cable-knit socks layered beneath the denim.
Shop the Look
- Polo Ralph Lauren The Iconic Cotton Chino Ball Cap
- Polo Ralph Lauren Oversize Fit Striped Cotton Shirt
- Polo Ralph Lauren Curved Tapered Jean
- Polo Ralph Lauren Calfskin Penny Loafer
- Polo Ralph Lauren Cable Knit Crew Socks
- Polo Ralph Lauren Polo ID Suede Mini Shoulder Bag
Look 3
(Image credit: Polo Ralph Lauren)
The Query: "Show me a casual-cool way to wear a barn jacket."
The Outfit: Finally, I focused on a fall trend that Ralph Lauren is excelling in: the barn jacket. I initially searched for styles and then refined my search to find outfits that revolved around the Cotton Utility Jacket. The brand’s signature preppy aesthetic appeared in the first styling suggestions, so I adjusted my keywords to better match my personal taste—like "minimalist,” "sleek," and "trend-forward"—to find a look I was eager to try on in real life. The result was based on the Curved Tapered Jeans paired with a heavyweight white T-shirt and Western ankle boots for a touch of edge. I was instantly enamored.
Shop the Look
- Polo Ralph Lauren Cotton Utility Jacket
- Polo Ralph Lauren Relaxed Fit Cotton Jersey Tee
- Polo Ralph Lauren Curved Tapered Jean
- Polo Ralph Lauren Leather Chelsea Western Boot
- Polo Ralph Lauren Polo ID Leather Mini Chain Bag
More Ralph Lauren items I want to style next:
- Polo Ralph Lauren Fringe Waxed Leather Jacket
- Polo Ralph Lauren Plaid Twill Paneled Shirtdress (a sophisticated take on autumn’s plaid trend
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I Tried Ralph Lauren's AI Stylist—Three Autumn Outfits It Selected for Me
From a wedding guest outfit to styling the classic Polo baseball cap, here’s how AI stylist Ask Ralph has styled me.