What AI Shopping Assistants Are and Why Retailers Care
An AI shopping assistant is a conversational, software-based agent that helps customers search, compare, and purchase products online by using natural language, personalised recommendations, and context from real shopping behaviour across the entire buying journey. For retailers, these assistants go beyond traditional search boxes and static filters, turning the online shopping experience into a dialogue where customers ask for ideas, constraints, and preferences in their own words. Instead of clicking through dozens of pages, shoppers can describe their needs—budget, style, size, or occasion—and receive curated options in seconds. This shift matters because retail AI technology is becoming a differentiator in a crowded ecommerce market, especially as large platforms set expectations for smoother, more intuitive checkout flows. By embedding AI directly into websites and apps, retailers aim to cut friction, reduce decision fatigue, and keep customers inside their own ecosystems rather than losing them to bigger marketplaces.
Kmart’s Joy: Virtual Try-On and ‘See It in My Space’
Kmart’s new AI shopping assistant, Joy, shows how retail AI technology can reshape product discovery and decision-making. Available on its website and app, Joy connects conversational search with visual tools: customers can try virtual try-on features for selected items and use a “See It in My Space” function to place furniture or décor into photos of their homes before buying. Joy acts as a virtual shopping partner that understands natural language, so a shopper can ask for a specific size, style, colour and budget and get tailored results in seconds. Customers can also upload their own photos to trigger more personalised recommendations and side-by-side comparisons. According to Kmart Group’s Chief Customer Officer Bernard Wilson, “customers aren’t just searching anymore; they’re engaging conversationally and looking for ideas and guidance,” and Joy is designed to meet that demand across Kmart, Target and marketplace brands in a single online shopping experience.
Amazon’s Agentic Shopping Assistant and the AWS Playbook
Amazon is turning its own AI shopping know-how into a product for other retailers with its Agentic Shopping Assistant on AWS. Built on Amazon Bedrock, AgentCore and OpenSearch, the solution gives retailers starter code, architecture guidance and expert support to launch conversational agents in weeks instead of years. The assistant is based on technology validated through “billions of real shopping interactions on Amazon.com” and insights from Alexa for Shopping, which combined Rufus and Alexa+ into a single agent. One quotable data point from Amazon: more than 300 million customers used its AI shopping assistant last year, generating nearly US$12 billion (approx. RM56.4 billion) in incremental sales. Retailers can adapt this foundation to their own catalogues, customer bases and brand voices, keeping their unique insights and relationships while riding on proven retail AI technology. The result is a plug-in path to sophisticated AI shopping assistants without building every component from scratch.
Kate Spade’s AI Gift Concierge and New Customer Journeys
Kate Spade New York is one of the first brands to apply Amazon’s Agentic Shopping Assistant, launching an AI Gift Concierge tuned to how people buy presents. Powered by Anthropic’s Haiku 4.5 model and informed by questions asked to Alexa for Shopping, the concierge holds natural-language conversations to suggest gifts by occasion, style and other cues. Tapestry, Kate Spade’s parent company, tested the assistant for around two and a half months before releasing it, positioning the tool as an answer to the stress many shoppers feel around gift buying. According to Amazon, internal data shows 53% of shoppers report stress when purchasing gifts, giving retailers a clear use case for more empathetic AI guidance. By keeping the experience focused on a specific mission—finding the right gift—the concierge demonstrates how AI shopping assistants can handle complex, intent-driven tasks that go far beyond standard product search or generic recommendations.
Competing with Marketplaces by Reducing Friction
Taken together, Joy at Kmart and Amazon’s Agentic Shopping Assistant show how AI shopping assistants are becoming central to online shopping experience strategy. Retailers are not only adding virtual try-on features and spatial visualisation, they are redesigning their customer journeys around conversation—whether that is browsing a full-range marketplace or narrowing down gifts for a specific occasion. These assistants reduce friction by compressing search, comparison and decision into a single dialogue, which helps retailers keep shoppers engaged instead of drifting to dominant marketplaces. At the same time, retail AI technology allows brands to encode their tone, merchandising rules and customer knowledge directly into the assistant, preserving differentiation. As more consumers grow comfortable using AI agents to shop, retailers that invest in their own assistants—rather than relying solely on external platforms—stand a better chance of owning loyalty, data and the all-important final step of checkout.
