Target rolled out an AI shopping assistant and announced a holiday strategy centered on affordability on October 21, 2026, anchoring its holiday retail push in affordability and exclusive brands to capture early shoppers.
Target is betting heavily on budget-conscious shoppers this season, pairing price reductions with an in-house digital assistant and an exclusive product lineup. The retailer announced that it expanded its holiday assortment to include 8,000 new items, with more than half exclusive to Target, including brands like Wondershop, Hearth & Hand with Magnolia, Threshold, and Threshold designed with Studio McGee. Most of the new items are priced at $20 or under, featuring many options under $5, alongside a $35 throw blanket, a $45 cashmere sweater, $10 pajamas, and $5 candles. Toys are a major focus for Target this holiday season, with the retailer adding 3,000 new items across its “fun101” assortment of toys, tech, gadgets, and fandom merchandise.
Price Cuts on Nearly 2,000 Everyday and Holiday Items
Ahead of the holiday shopping rush, Target slashed prices on nearly 2,000 apparel, footwear, accessories, and home products on September 29, 2026. These reductions follow more than 10,000 price drops implemented over the prior year.
Among the specific price cuts, women’s long-sleeved tees dropped 20% from $15 to $12. Average prices for women’s shoes fell from $40 in 2025 to $35, which marks a 12.5% reduction, while nearly 70% of new women’s shoe styles are lower-priced. Children’s rain and winter boots are approximately 15% cheaper on average compared to 2025, bedding prices are down about 15% on average with some items priced at least 20% below comparable items last year, and Threshold queen comforters fell from $89 to $69. Price comparisons show savings of up to around 22.5% across items. Target chief merchandising officer Cara Sylvester and CEO Michael Fiddelke outlined the retailer’s approach during an October event in New York, where Sylvester and senior vice president and chief brand officer Michelle Mesenburg discussed marketing strategies including the Academy of Giftology
holiday campaign aimed at building gift-giver confidence.
Value plays an important role all year, especially so during the holiday season.
Michael Fiddelke, Target CEO
Ask Target Launches as Conversational AI Enters the Holiday Rush
Target joined a growing field of major retailers by launching a beta version of its AI-powered chatbot, called Ask Target, on Target.com and the mobile app. The conversational tool allows shoppers to find inspiration, build wishlists for themselves and others, and ask general questions about merchandise rather than relying simply on keyword searches.
Retailers are turning to proprietary in-house bots trained on proprietary in-house data rather than generic models to handle specific product queries, building on tools like the Buy Again feature that uses AI-driven personalization to surface frequently purchased items and past purchases, alongside a list-scanning feature in the digital holiday catalog and a shopping experience inside ChatGPT.
We have seen a lot of traction as we start to think about that conversational AI, so the team was excited to push it through to capitalize on our biggest season of the year.
Cara Sylvester, Target Chief Merchandising Officer
Target also deployed ChatGPT Enterprise across its roughly 18,000 corporate employees for supply chain forecasting and store operations, while store employees utilized an internal rollout of Ask Target to brush up on new merchandise, particularly in the new Beauty Studio department.
Early Holiday Strategy Faces Broader Industry Forecasts
Target’s September price cuts and daily promotions aim to capture spending before traditional late-November peaks. Deloitte’s 2026 holiday retail survey found that 79% of respondents expected holiday items to cost more than last year and planned to spend $1,654 on average, up approximately 4% from 2025. Furthermore, 22% of consumers planned to shop early in 2026, with respondents expecting to spend roughly 28% of their total holiday budgets by the end of October, marking the highest holiday budget portion in six years.
This year’s forecast reflects our confidence that consumers will prioritize the holiday season even as they remain mindful of their budgets.
Matthew Shay, NRF President and CEO
Target plans to run a new Deal of the Day each day from November 1 through December 24, alongside early Black Friday deals scheduled for November 5 through 7, while continuing to offer a standing policy allowing shoppers to request a price adjustment if an eligible item drops in price within 14 days of purchase.
Journalists Nicholas P. Brown in New York and Sanskriti Shekhar in Bengaluru reported on the strategy announcement, with editing by Sahal Muhammed.