Consider the following:

• A beauty brand selling a single lipstick vs. a beauty routine.
• A furniture brand selling a single chair vs. a styled room.
• Buying a single stock vs. a managed portfolio.
• Booking a flight vs. a curated itinerary.

And in the case of apparel, selling a single item (tops) vs. a lifestyle or a persona or even a moment (Tuesday mornings).

These are the things that I thought about as I explored Ralph Lauren’s new styling tool, Ask Ralph. The tool serves up styling inspiration via complete outfits tailored to user prompts. Ideally, Ask Ralph serves up ready to shop looks that are curated by the merchandising team.

As a former Ralph Lauren merchant myself, I built “outfit stories” so every product could pair with a seasonless key item, a coat, a seasonal handbag, or anchor style. Doing that made it simpler for visual merchandisers, brand ambassadors, and customers to assemble complete looks.

Let’s take a moment here to talk about two different approaches to assortment planning.

One for selling single items and the other for “outfitting.”

1) Category-Buyer Model (CBM): A key-item approach that balances depth (options within a category) and breadth (number of categories). Shoppers tend to buy one item at a time. Department and specialty retailers often use category buyers (e.g., women’s sweaters, men’s denim). Outfits are an afterthought, so storytelling is fragmented.

2) Outfit-Based Model (OBM): This starts with collections and complete looks, then links key items (tee, core denim) back to anchor pieces (blazer or cardigan). The story is cohesive, selling a persona, a lifestyle or a moment.

The intention is to guide customers to purchase full looks thus lifting units per transaction.

In other words, not selling tops but selling “Tuesday morning.”

Shifting from items to outfits changes how customers shop and drives profitability.

Naturally, the best apparel brands know this:

• Ralph Lauren sells a lifestyle across apparel, footwear, accessories, and home.
• Levi’s has expanded beyond jeans to full looks that turn occasional denim buys into wardrobe refreshes.
• Zara consistently merchandises themed outfit sections with shoes and handbags nearby, making head-to-toe styling effortless

If we go back to the opening examples: beauty routines, styled rooms and managed portfolios win over single lipsticks, chairs and stocks.

Now you might say “Big whoop, you’re just talking about rather obvious and simple concepts of upselling/cross-selling.”

But, “simple to do” does not equal “easy to do.”

Outfitting demands tight alignment across merchandising, marketing, and store ops. If the floor is chaotic, the story dies. If marketing and merchandising tell different stories, the customer is confused.

But, it get more interesting…

Think agentic commerce. OpenAI’s Agentic Commerce Protocol/Instant Checkout enables single-item purchases inside ChatGPT. Multi-item carts are close behind. AI stylists like Ask Ralph will multiply and should recommend full looks, not lone SKUs.

However, these tools will only be as strong as the merchandising proficiency of the brand.

If merchandising strategy and execution are broken, you can’t slap agentic AI on top and hope to gill the gap, it’s not Flex Seal.