A Grab Bag of Opportunities: Big Retail Trends for 2026

What do agentic shopping agents, U.S. trade policy and tariffs, circularity, rising mall visits, Gen Alpha’s use of Discord and YouTube Shorts, and endless aisles have in common?

It’s not a trick question. Each of these developments will have potentially substantial implications for retailers and their tax teams in 2026. These trends, along with many others, were scrutinized and stress-tested at Retail’s Big Show, the massive trade show the National Retail Federation stages each January.

Not surprisingly, AI-related developments feature prominently among trends shaping retail’s future. While many of us are familiar with tariff-related challenges and endless aisles (which I first mentioned a couple of years ago during our Black Friday and Cyber Monday coverage), the other trends I listed warrant a bit of context.

Agentic shopping agents act on behalf of shoppers – and by “act,” I mean these systems can compare, select, negotiate, and transact based on guardrails established by the consumer.

Circularity refers to the extension of product lifespans and the related reduction of waste stemming from the reuse, resale, and recycling of products. “Circular retail solutions will expand in 2026, driven by consumer demand, economic constraints, and regulatory requirements,” notes NRF Vice President of Corporate Social Responsibility and Sustainability Scot Case.

Trends with Tax Implications 

These inventory and pricing adjustments have implications for tax determinations, of course. So do at least two other 2026 retail trends.

Let’s start with the blending of in-store and online sales, also known as “phygital”– the fusion of physical and digital shopping experiences that support a seamless, integrated customer journey. Think QR codes, BOPIS and BORIS, in-store kiosks, and cashless/cashier-less checkout. Each channel in this multi-dimensional customer journey triggers unique sourcing rules and tax rates. The cross-platform integration that supports these phygital capabilities can obscure the transaction chain, making nexus determinations and, in some cases, marketplace facilitator obligations difficult to perform and identify quickly and accurately.

The growing use of multi-platform social media purchasing also poses tax compliance challenges. As shoppers (especially those in the Gen Z and Gen Alpha segments) expand beyond TikTok to YouTube Shorts, Discord, and Meta Reels, retail tax teams must contend with different marketplace models, most of which come with varying degrees of facilitator responsibility. When retailers sell through multiple social channels simultaneously, they must continue to track taxability, apply correct rates, and maintain proper documentation with sustained accuracy and speed.

Tax Technology Stacks Must Keep Pace 

It’s tempting to refer to the sheer volume, variety, and in some cases, uncertainty of current retail trends and developments as a “mixed bag,” but that doesn’t do the benefits of these opportunities justice. In 2026, retailers and e-commerce companies will have a plentiful grab bag of innovations, growth levers, and resilience-enablers at their disposal. 

And it will be up to tax teams to understand the compliance implications of these mechanisms while ensuring their tax technology stacks can keep pace with scalability needs, more dynamic price and promotion changes, new supply chain scenarios, and geographic expansion.