When the Christmas season meets artificial intelligence, the holiday shopping experience is undergoing a silent revolution. Over the past year, shopping assistant chatbots have evolved from novelties to ubiquitous standards. The Christmas of 2025 sees AI technology deeply integrated into every aspect of holiday preparation—from finding the perfect gift and virtual try-ons to automated purchasing and inventory checking. Technology is simplifying our holiday season in unprecedented ways.
1. Retail Chatbots: Conversational Shopping Experiences
This Christmas season, major retailers have rolled out AI shopping assistants. Amazon's Rufus, Walmart's Sparky, Target's seasonal gift finder chatbot, and Ralph Lauren's "Ask Ralph" style recommendation assistant, developed in partnership with Microsoft, all offer users a more natural shopping method. Unlike traditional keyword searches, these chatbots allow you to describe your needs through conversational interaction, much like talking to a friend.
For example, you could ask, "Find a Christmas gift for my dad who loves hiking, budget around $150," and the bot would synthesize product information, reviews, and occasion suitability to recommend appropriate options. Target's gift finder chatbot is even designed specifically for the holiday season and is only available during Christmas. This personalized service makes the process of finding the perfect gift more efficient and human-centric.
2. Cross-Platform AI Shopping Research Tools
If you prefer not to limit yourself to a single retailer's website, tech platforms offer AI tools that can simultaneously search multiple sites, providing a broader selection. OpenAI recently added a "shopping research" feature to ChatGPT, offering personalized buying advice for products heavy on detailed specifications, like electronics or appliances. This feature activates when you ask a shopping-related question in ChatGPT or manually turn it on in the chat window.
Google users can get a similar experience when using its search engine in AI Mode. A recent major update for shopping searches allows users to describe what they're looking for as if talking to a friend and receive an "intelligently organized response" based on 50 billion product listings, complete with pictures, prices, reviews, and inventory information. Google added similar shopping features to its Gemini AI chatbot app for U.S. users last month.
Meanwhile, Perplexity unveiled its own shopping assistant feature last week, which can tailor recommendations based on previous search history. The common thread among these tools is their ability to understand natural language queries and provide recommendations better aligned with individual needs.
3. Generative AI "Try On" Tools
Found a stylish cardigan for your partner but unsure about the fit or silhouette? Generative AI "try on" tools let you visualize how clothing might look when worn. Traditional virtual fitting room tools relied on complex 3D rendering, actual photo shoots, and augmented reality, often limiting users to selecting a model that best matched their body type to preview clothing.
Now, Google is leveraging AI to allow shoppers to virtually try on garments and shoes using photos of themselves in simple poses. Using this feature (available via Google's shopping desktop search and mobile app in Australia, Japan, Canada, and the U.S.) is simple: just tap the "Try it on" button on a product photo and add a full-length photo of yourself. You can then save the image with the tested item or share it. The original photo is also saved to your account, so you don't need to keep uploading new images.
Google states that if shopping for someone else, you can upload their photo, but you must have their permission. Currently, accessories like hats or jewelry, swimwear, and lingerie are exceptions and not supported.
4. Duolingo & Headway: Getting a Head Start on New Year's Learning Goals
The Christmas season isn't just for shopping; it's also a time for planning New Year's self-improvement. The language learning app Duolingo broke into the top 3 of the U.S. iOS overall paid charts on the last day of 2024, achieving its best performance of the year, with its in-app purchase revenue for that day nearly four times the usual amount. Headway, which focuses on "reading a book in 15 minutes," entered the overall paid top 100 charts in the first week of the new year.
The holiday success of these apps reflects a common user mindset: "The trio for restarting life consists of exercise, learning a language, and reading". As the festive atmosphere pushes emotions to a peak, people begin considering how to make changes in their lives, and various "life-changing little tools" become the most direct choice.
5. Habit Tracking Apps: Building Better Holiday & New Year Habits
The holiday season is also an excellent time to cultivate new habits. Habit-tracking apps like "Me+" and "Finch" both see download peaks around January 1st, indicating many users are trying to add one or two better habits for the new year. Finch is particularly interesting as it gamifies habit tracking, motivating users to stick to daily goals by caring for a virtual bird. This lighthearted, fun approach is especially suited to the holiday atmosphere, making self-improvement feel less like a daunting task.
Looking ahead, AI's role in holiday shopping will deepen further. We can anticipate more accurate personalized recommendations, more realistic virtual try-on experiences, and more intelligent gift planning systems. Potential developments include: gift recommendations integrated with health data (like suggesting suitable fitness gear for health-conscious friends/family), AI suggestion optimization based on past gift feedback, and cross-platform gift coordination systems to prevent duplicate gifts among family members.
The technological innovation of the Christmas season not only makes holiday shopping more convenient and efficient but, more importantly, frees up our time and energy to focus on the true meaning of the holidays—spending quality time with loved ones. When AI handles the tedious processes of finding gifts, comparing prices, and making purchases, we have more space to enjoy family gatherings, traditional celebrations, and warm moments.
This Christmas, why not try some AI-driven apps and experience how technology can inject new magic into ancient traditions? From conversational shopping assistants and virtual fitting rooms to automated price tracking and smart inventory inquiries, these tools are redefining our holiday experience. After all, the holidays bring not just lively gatherings and countdown rituals, but also the courage for a fresh start. And when this courage meets the most advanced technology, the holiday season becomes more exciting, more personalized, and filled with greater possibility.
