This AI chatbot will give you style advice… and attitude

Pick a bot version of Kim Kardashian or Anna Wintour as your personal celebrity shopper and build a wardrobe based on their distinctive style, or your own.

My first attempt to get style advice from a new fashion chatbot called ShopWithAI was not great. I was thinking oversized fedora: who could give me better advice than a man known for his impeccable hat taste, the musician and fashion icon Pharell Williams himself?

Williams is one of several “digital personas” available to choose from on the website. Others include Kim Kardashian for a full-on beige experience, a “perfectly preppy with the ‘90s sloppy twist” John F Kennedy Jr, and Princess Diana, a “champion of high-low dressing.”

I stuck to Williams, and the chatbot suggested typing in things like “I want men’s green fatigue pants” and “Show me dope red sneakers.” Suppressing my inner shopaholic, I focused on fedora recommendations.

Unfortunately, my interaction with the ‘Williams-bot’ went nowhere. I get rebuffed – twice! – with a frosty “Hey, I’m busy chatting with a lot of other people” and “Please try again in a few seconds.”

Forget it, I thought, I’ll find someone else.

So I scrolled through the celebrity selection and saw Lenny Kravitz for “effortless” rockstar looks and Justin Bieber for a “laid back, slouchy, west coast style.” Passing them by, I opted for Anna Wintour, the steely editor-in-chief of Vogue, and got better luck this time. After all, people tend to respond well to those who are sure of what they want.

I asked for the same thing – an oversized fedora – and was shown eight wide-brimmed hats to pick from, ranging from budget-friendly to splurge-worthy. Clicking on the one I liked most, the page redirected me to an online shop selling the product.

I could also “heart” what I love, press a thumbs-down for things I didn’t, or go for the “more like this” option to get other recommendations. The virtual shopping assistant also offered me a chance to view “related racks” – more specific search suggestions such as “oversized fedora with feather.” Which I didn’t know I wanted, but now maybe I do?

If I sign up, I am promised my “own shopping assistant that knows your personal style.” Based on earlier recommendations, things I like, and saved chat histories, ShopWithAI should ‘learn’ about my taste enough to select just the right things from thousands of brands online, including clothes, accessories, and decor items, potentially saving hours of browsing.

The chatbot will not engage in much small talk, gently diverting all attempts at irrelevant chitchat back to the matter at hand, which is to offer you style guidance and make you buy stuff.

Conveniently, I can also upload a picture and get recommendations based on that, because a “picture is worth a thousand words,” according to ‘AI Wintour,’ who can also pick me a “fun cocktail necklace” and some “conservative floral dresses for work.”

My outfit for the next work meeting is sorted, then.