May Retail Roundup

The proof is always in the pudding, and May just served it.

May is my favourite month. It sits in that perfect in-between; not quite spring, not quite summer, but something is shifting and you can feel it. There's always this energy to May and in 2026, you can sure feel it. As it turns out, that's exactly what happened in retail this month too.

We're past the point of talking about transformation and not quite at the other end where everyone's claiming they nailed it. We're in the messy, honest middle which, let's be fair, is pretty much always where the most interesting things happen if you know where to look.

So. Let's look.

Women ran the numbers. And I'm going to keep saying this until people stop acting surprised.

Hillary Super at Victoria's Secret nearly doubled EPS expectations. Kecia Steelman at Ulta posted 11% net sales growth and beat estimates by 12%. Kruti Patel Goyal delivered early turnaround signs at Etsy just four months in. Molly Watkins stepped up to CEO of Sam's Club. Sharon Price John moved to Carter's. Ann-Marie Campbell led Home Depot's fulfilment transformation with barely a headline to show for it.

I could frame this as "great month for women in retail leadership" and move on. But can we just stop treating women's leadership as the warm-up act already? What May actually showed is that the retailers performing most consistently right now are disproportionately led by women who inherited difficult situations and chose to fix the fundamentals rather than refresh the narrative around them. #Boss

Is the industry connecting those dots yet? Not loudly enough. Call it what it is, readers. This isn't a diversity story. It's a performance story. And quite frankly, it's about time we talked about it that way.

AI is growing up. Which means it's getting less glamorous and considerably more honest.

Here's the theme I keep coming back to in 2026: the gap between talking about doing something and actually doing it is getting harder to hide.

Nowhere is that more true than AI.

Amazon retired Rufus and launched Alexa for Shopping, a full agentic assistant that tracks price history, builds shopping guides and handles routine purchases across multiple retailers. Shopify hit $100 billion in GMV for the second consecutive quarter. Etsy went live inside ChatGPT. The pace of agentic commerce is moving faster than most retailer roadmaps planned for and I'd wager most aren't ready for what that actually means for how customers discover and buy.

And then Starbucks switched off an AI inventory tool that had been running across North American stores. It kept miscounting and mislabelling. So they just turned it off.

Good. That is the right call. But I'd ask the question nobody seems to be asking loudly enough: how many retailers right now are keeping a broken tool running because it looks good in the board update? I suspect the answer is more than a few.

AI works when it solves a real problem cleanly. The question worth asking of every single AI investment right now is not "are we using it?" It is "does it actually work?" Turns out those are very different questions.

The consumer said one thing and did another.

Some things never change, do they?

You know that friend who says every Sunday they're starting fresh on Monday; new routine, new habits, whole new chapter... and then Monday comes and, well, life happens? That's the US consumer right now. Record low sentiment. Two thirds saying they're cutting back. And then Walmart posts $177.8 billion in Q1 revenue and Target grows net sales 6.7% and Shopify merchants move $100 billion in a single quarter.

I'm not laughing at the contradiction. I'm saying it's data and it's telling us something specific if we stop calling it "resilience" long enough to actually look at it.

Consumers are not spending broadly. They are spending precisely. They know what they want, what they will pay, and they have very little patience for anything that makes it complicated to get there. Walmart reaches 60% of the US in under 30 minutes. Target's same-day delivery grew 27%. That is not resilience, my friends. That is infrastructure meeting intent.

The retailers with friction in the path to purchase are going to feel it. Probably not this quarter. But I'd mark Q3 in your calendar.

The Shein and Everlane deal. You genuinely cannot make this stuff up.

Shein acquired Everlane for approximately $100 million. The world's fastest, most scrutinised, most everything fast fashion brand bought one of the most values-led labels in US apparel. Everlane stays independent. Keeps its sustainability commitments. Shein says it won't interfere.

The irony is a little perfect, right?

The easy take is greenwashing by acquisition. Roll your eyes, write the headline, move on. But I think that reading is lazy, and I think Shein knows exactly what it is doing. This is not about Everlane's supply chain or its margins. It's about trust. In a market where consumer trust is becoming a genuine structural advantage, Shein just bought a brand that has it.

Whether that trust survives contact with the parent company is, of course, the rather large question sitting in the middle of this deal. I'd give it 12 months before the Everlane customer tells us the answer. And they will tell us, loudly, one way or another.

Watch this one. It matters more than the price tag suggests.

The C-suite kept moving. Faster than feels entirely comfortable.

Walmart lost two senior executives. Starbucks cut 300 corporate roles. Lululemon's incoming CEO Heidi O'Neill is already facing activist pressure from Chip Wilson before she has even started. Well. That's a welcome gift now isn't it.

Saks Global emerged from bankruptcy with a leaner team and some rather ambitious GMV targets. Which, you know, good luck to them. Genuinely.

Here is what I think is happening beneath the headline churn: the retailers who overhired during the pandemic growth years are now rebuilding. And the ones doing it with a clear point of view about what kind of organisation they are becoming are cutting very differently from the ones doing it because the CFO said they had to. The former looks like strategy. The latter looks like panic. Both look the same in a press release.

The difference shows up in results two or three quarters later. I'd be watching Q3 and Q4 very closely this year.

So what was May, really?

Retail is still about people. The people running the business, the people walking through the door, the people deciding at 11pm on their phone whether your product is worth it. That has not changed and it will not change regardless of how many agentic commerce announcements we sit through.

What May showed is that the retailers winning right now have figured out something that sounds simple and is actually very hard: they know what they are doing, they know who they are doing it for, and they have built the infrastructure to deliver on that promise at speed.

The women leading the strongest results this month did not get there by talking about fundamentals. They fixed them. The AI tools earning their place did not do it by sounding impressive. They worked. The consumer did not reward loyalty or nostalgia or a good brand story. They rewarded convenience, precision and trust.

We know all of this, of course. We have known it for a while. But May made it very difficult to keep pretending otherwise. And quite frankly? It is about time.