# Conversational Shopping Assistants Macy’s New Ask Macy’s Chatbot Launches on Gemini By Kanesa David | Written with AI assistance | Published 2026-04-09 | Tech Source: Trend Hunter, https://www.trendhunter.com/trends/ask-macys References: [retaildive](https://www.retaildive.com/news/ask-macys-AI-conversational-shopping-assistant/815928/) & [macys](https://www.macys.com/)  Macy’s launched Ask Macy’s, an AI conversational shopping assistant powered by Google Gemini that helps shoppers discover brands and receive personalized product recommendations, featuring a virtual try-on capability. The tool debuted after an internal dark launch and beta testing that gathered employee feedback on tone and practicality. Ask Macy’s prompts customers to describe needs like budget, occasion, color, style and size, then curates options rather than returning literal search results; it also displays a notice that the AI is learning and may err. The assistant rolled out across Macy’s digital platforms, including its app, on March 23. For consumers, Ask Macy’s streamlines discovery and personalization inside one chat-driven flow, increasing engagement and revenue per visit during beta. Its emphasis on curated suggestions reflects a broader retail trend toward conversational commerce that blends discovery, personalization and virtual try-on experiences. Image Credit: JHVEPhoto / Shutterstock ## Trend Insights (Trend Hunter) - Score: 3.1/10 - Popularity: 9% | Activity: 14% | Freshness: 71% - Audience gender: 50% men, 50% women - Primary generations: Millennial, Gen X - Top markets: North America ## Categories [Trend Hunter](https://www.trendhunter.com/trends) > [Tech](https://www.trendhunter.com/tech) > [AI](https://www.trendhunter.com/ai) ## Key Themes ### What's Driving This Trend - **Conversational Commerce:** chat-driven shopping flows that combine discovery, personalization and transactions create opportunities for embedded commerce experiences that reduce friction between browsing and purchase. - **AI-powered Virtual Try-on:** virtual try-on capabilities linked to conversational interfaces enable more confident purchase decisions by simulating fit and appearance across diverse body types and styles. - **Curated Recommendation Engines:** recommendation systems that prioritize curated, context-aware suggestions over literal search results can increase engagement and average order value by surfacing complementary and discovery-driven items. ### Who This Affects Most - **Retail:** store and omnichannel retailers stand to be disrupted by conversational assistants that transform storefronts into personalized, interactive experiences blending discovery and checkout. - **Fashion-tech:** companies at the intersection of apparel and technology are positioned to redefine fit, returns and design feedback through integrated virtual try-on and AI styling capabilities. - **E-commerce Platforms:** platform providers could be reshaped by embedded AI chat layers that alter merchandising, search economics and merchant tools through higher personalization and conversion rates. ## Related on Trend Hunter - [AI Grocery Assistants](https://www.trendhunter.com/trends/albertsons-3.md) - [AI Chat Shopping Systems](https://www.trendhunter.com/trends/ai-chat-shopping-systems.md) - [AI Shopping Integrations](https://www.trendhunter.com/trends/sephoras-chatgpt-app.md) - [AI-Powered Shopping Companions](https://www.trendhunter.com/trends/ai-powered-shopping-companions.md) - [Multi-App AI Assistants](https://www.trendhunter.com/trends/chatgpt-integrations.md) - [AI-Powered Shopping Tools](https://www.trendhunter.com/trends/target-7.md) - [Deal-Finding Chatbot Features](https://www.trendhunter.com/trends/chatgpt-shopping-assistant.md) - [AI Product Design Assistants](https://www.trendhunter.com/trends/arcade-maia.md) - [Family-Friendly AI Shopping Assistants](https://www.trendhunter.com/trends/duckymaze.md)