The holidays are a make-or-break moment for retailers. But this year, the real competition isn’t just about who has the best deals — it’s about who has the best tech.

For 2025, it's projected that more money will be spent online than in-store, marking a major turning point for the retail industry. From AI-driven shopping assistants to dynamic gift guides and connected stores, technology is rewriting the rules of how we shop, spend and celebrate.

Together, these shifts point to a single truth: The future of holiday shopping isn’t about where it happens, but rather about how seamlessly it happens.

Artificial intelligence is taking center stage in this year’s holiday shopping season, and big box retailers are behind some of the most ambitious pushes.

For example, Walmart unveiled a new partnership with OpenAI that allows customers to shop on Walmart directly through ChatGPT. This move is part of Walmart’s larger push to weave AI into every part of the shopping journey, bringing chat-based shopping together with the app’s new smart features.

Those tools range from simple perks like in-store savings alerts and real-time aisle finders to more immersive experiences, like wish lists and 3D or augmented-reality previews that let shoppers see décor and gifts before they buy.

Together, these advances signal a shift away from traditional “search and scroll” shopping toward more dynamic, personalized assistance where consumers can ask for what they need in natural language and get curated recommendations in return.

The move also reflects a wider industry trend: As AI assistants become more context-aware and multimedia-driven, retailers are racing to build experiences that feel both intuitive and individualized. For shoppers, that means less time toggling between tabs and more time getting exactly what they’re looking for.

Behind every smooth checkout and real-time inventory update is something shoppers rarely think about: the network that keeps it all running.

This holiday season, retailers are leaning on smarter, faster connectivity to make shopping feel effortless, whether that’s secure mobile checkout, live inventory updates, or Wi-Fi strong enough to handle crowds of connected shoppers. Many stores are upgrading to flexible, cloud-based networks (known as SD-WAN) that can handle big spikes in traffic and keep data flowing between stores and warehouses without a hitch.

It’s what makes today’s connected experiences possible — from virtual fitting rooms and “magic mirrors” that suggest outfit pairings to in-store beacons that turn shopping into a kind of game. The right network can even help retailers manage voice and video tools that keep staff connected across locations and ready to help customers in real time.

In short, the real magic of modern retail is more than just what you see on the shelves, but also the invisible web of technology powering it all behind the scenes.

At the same time, the humble gift guide is getting a high-tech upgrade. Once a static list of editor picks, gift guides are now dynamic, data-driven discovery engines powered by AI and personalized for every kind of shopper.

Retailers and marketplaces like Lyst are combining algorithmic insights with human curation to surface gifts that match not just demographics, but intent and behavior. Last year’s most-clicked guide on Lyst, for instance, highlighted “subversive statement gifts” — think tongue-in-cheek fashion pieces like a pigeon-shaped handbag or bold, conversation-starting accessories that doubles as art.

Behind the scenes, AI tracks price changes, inventory levels and trending search terms to keep guides up-to-date in real time. As one industry expert put it, mentions in these guides now act as “signals” that can shape how AI surfaces brands across search and shopping platforms.

Going forward, today’s placement in a gift guide could influence next year’s visibility in a shopper’s AI-powered search results.