As AI reshapes how consumers discover and buy products, retailers are racing to adapt — even using AI to understand AI itself. According to experts from Wharton and Columbia, generative AI has transformed traditional shopping behavior, replacing keyword searches with personalized, conversation-driven recommendations. Retailers like Target are revamping their e-commerce strategies to ensure products surface in AI chatbot queries, while others experiment with “GEO” (Generative Engine Optimization) to boost visibility in tools like ChatGPT and Gemini. The shift is also fueling innovation in digital consumer personas and AI-driven content creation, though challenges around bias and transparency persist. As one expert put it, the retail playbook isn’t just being rewritten — it’s being reprogrammed.

Despite the rise of e-commerce, in-store shopping remains a cherished holiday tradition for most consumers. According to Quad’s 2025 holiday survey, 74% of shoppers say browsing in stores helps them get into the holiday spirit, and 76% call it a holiday ritual. Shoppers — especially Gen Z — value the joy of discovery, with two-thirds saying their favorite gifts came from in-store finds. The survey also revealed waning enthusiasm for Black Friday, with 84% of respondents preferring meaningful deals spread throughout the season instead of one-day events. For brands, it’s a clear message: the magic of retail still lives in the aisles.

Despite a wave of retail closures and bankruptcies, U.S. retail fundamentals remain strong, according to Colliers’ Q3 2025 Retail Market Statistics report. The national vacancy rate held steady at 4.3%, supported by robust absorption, limited new supply, and solid rent growth. Southern and Western metros like Miami, Dallas, and Phoenix continue to lead the market, driven by income and population growth. With rent averages rising to $25.53 per sq. ft. and construction activity focused on smaller build-to-suit projects, the retail sector is showing remarkable resilience heading into the holiday season.

This holiday season, millennials and Gen Z are leading the charge in using AI and chatbots for shopping, with 44% of millennials and 42% of Gen Z planning to rely on these tools for gift ideas, price comparisons, and product recommendations, according to an Epsilon Pulse report. ChatGPT is the preferred AI tool for 93% of Gen Z shoppers. Social media also plays a major role, with TikTok, Instagram, and Facebook serving as key sources of holiday inspiration. While Amazon remains the top shopping destination, discount and department stores are seeing strong seasonal interest as consumers balance convenience, inspiration, and deals.

Southeastern Grocers is reintroducing itself as The Winn-Dixie Company in early 2026, positioning as a “brand-new 100-year-old company” rooted in Florida and southern Georgia. The grocer is refocusing on its home market while transitioning ownership of stores in Alabama, Louisiana, and Mississippi. As part of its Florida expansion, Winn-Dixie will acquire and convert three Hitchcock’s Markets and launch new store formats, remodels, and expanded liquor stores. The company also plans to revive fan-favorite products like Lip Lickin’ Chicken and expand online grocery delivery partnerships with DoorDash and Amazon. With around 270 total stores planned under the unified brand, Winn-Dixie aims to celebrate its legacy while modernizing for the next century.

Miami’s office leasing market is heating up, with over 500K SF of leases signed in Q3, marking a 200K SF jump from the previous quarter and putting the city on track to surpass 2024’s total leasing volume. Despite early-year uncertainty tied to new global tariff policies, companies regained confidence, closing major deals in the second half of 2025. Top leases included Stearns Weaver Miller’s 97K SF at Museum Tower and ADP’s 78K SF at Miami Waterford Business District. With vacancies tightening in submarkets like Brickell (13.4%) and Coconut Grove (just 3.1%), and rents holding near record highs—up nearly 7% year-over-year—brokers expect Miami’s momentum to carry into Q4 and beyond.

CVS Health has officially expanded its footprint in the Pacific Northwest, completing the acquisition of 63 Rite Aid and Bartell Drugs stores across Idaho, Oregon, and Washington. The deal, finalized after Rite Aid’s bankruptcy, also includes the prescription files of 626 locations in 15 states and the hiring of over 3,500 former Rite Aid employees. CVS says the move will strengthen access to pharmacy care for nearly 9 million new customers and bolster its presence in local communities through targeted store investments and enhanced training programs. As Rite Aid exits the retail landscape following its second bankruptcy in two years, CVS solidifies its position as one of the leading pharmacy providers in the U.S.

Dollar Tree struck an optimistic tone at its annual Investor Day in New York, projecting a 12% to 15% compound annual growth rate in earnings per share from fiscal 2026 to 2028. The forecast reflects stronger profitability following the sale of Family Dollar for $1.01 billion and reduced costs tied to tariffs, pricing conversions, and distribution issues. The retailer reaffirmed its 2025 outlook, reporting 3.8% same-store sales growth and a $271 million stock buyback so far this quarter. CEO Mike Creedon described this as a “new chapter” for the company, emphasizing innovation, assortment flexibility, and a bold long-term vision to grow the Dollar Tree brand across North America.