How an AI cap became a storytelling masterpiece

 We love a good hat.  

Whether it be an Aperol Spritz summer bucket hat or a cap that’s been to space, if it’s something that can be worn on your head (and branded, of course), then we’ll love it.

You might even say we’re cap-tivated by them (sorry!).

And this time, the cap that’s got our heads turning is one launched by Anthropic, the company behind the AI chatbot Claude.

Now, hear us out. I know you hear ‘AI’, and you think snorefest. But, whilst everyone was mourning the em-dash and complaining about slop as if they were back in the school dinner queue, Anthropic were changing the way we think about AI, one free coffee and branded hat at a time.

In this post, we’ll explore why the Anthropic Claude pop-up was such a success and how the whole brand story surrounding the event relied on a single branded hat.

Want to see what you could do with a hat? Check out our full range of branded hats, caps and more headwear essentials below.

In short…

Anthropic's "Keep Thinking" pop-up gave away free coffee and a plain dad hat embroidered with a single word: thinking - and the internet lost its mind. Over 5,000 people queued, 10 million social impressions followed, and at least one person switched AI providers based purely on vibes. Here’s how a hat did what no product demo could.

What is Claude, and who are Anthropic?

Claude is like ChatGPT, but where ChatGPT may have been your first AI date, Claude is the one you’ll fall in love with.

Anthropic, the company that owns Claude, is one of the leading brands in the AI market. It holds a 32% market share and over 300,000 customers, which, according to Menlo Ventures, is ahead of OpenAI's (the company behind ChatGPT) 25% share.

Its revenue also grew from under $1 billion at the start of 2025 to over $5 billion by August of the same year.

But unlike others in the industry, Claude hasn't scaled through gimmicks or going viral for all the wrong reasons.

Instead, it's leaned into thoughtfulness, creativity, and judgement.

It’s a thought companion rather than a quick fix. Claude will take you through its workings so you can get to grips with what it’s found.

It’ll show you the ropes so you can take the lead.

And that’s what the crux of Anthropic’s ‘Keep Thinking’ pop-up campaign was all about.

Read more: AI vs merch: which is a better tool for long-term brand building?  

It’s time to put your thinking cap on

This thinking all came to a head (...) last October when, for seven days, Claude resided at Air Mail's newsstand in the West Village.

Now Air Mail isn’t just any newsstand. Founded by former Vanity Fair editor Graydon Carter, the space is chic, literary, and downright cool (without even trying, you know?).

It’s a place you’d go for a coffee, to sit, read a magazine, to think. It’s suave and sophisticated. An old Italian man drinking an espresso in the corner wouldn’t look out of place.

It was the perfect location to host Claude’s pop-up - and the internet absolutely lost its mind.

Over 5,000 people queued up, there were 10 million social media impressions over a single weekend, and one attendee waited for over an hour and a half in line, posted about it online, then announced he was switching from a rival AI tool to Claude "on vibes alone."

Visitors who showed the Claude app on their phones got free coffee and a "Thinking Cap." A plain dad hat, embroidered with just one word: thinking.

That's it. That's the product.

There were also tote bags, postcards, matchbooks and coffee cups decorated with art from Anthropic's in-house illustrator, plus printed copies of CEO Dario Amodei's 50-page essay, Machines of Loving Grace, “wrapped in navy cloth and printed on locally sourced, 100% post-consumer recycled paper”.

Cute.

Not a product demo. Not a sales funnel. Just: here's coffee, here's something to read, here are some things to hold. Think for a bit.

The campaign later extended to London, landing on Chiltern Street in Marylebone with limited festive-edition green and red hat drops, bringing the same calm, intentional energy across the Atlantic.

Paddington would have been proud.

So, why did it work so well?

Claude turned a hat into a storytelling masterpiece (along with a few extras). Here’s how:

1. They stopped selling features and started selling identity

Claude is impressive, but is it queuing-for-two-hours-impressive? No.

That’s because people weren’t queuing for Claude (not really); they were queuing to be a part of something.

Because, deep down, doesn’t everyone want to be someone who’s thought of as thinking deeply?

And that’s exactly what the “Thinking Cap” does. It signals that the wearer is smart. Sophisticated. Knows about what’s going on.

And the cap tells the world, in a single moment, who you are, and it’s someone everyone wants to be.

That right there is identity-led branding, and it's super hard to replicate.

2. The merch had meaning

Here's the thing about branded merchandise that often gets misunderstood: giveaways that are too heavily branded come across as marketing.

Merch with meaning instead comes across as culture.

The "Thinking Cap" walks that line perfectly.

It's minimal, it's wearable, it's cool - and it's tied directly to Claude's entire brand positioning.

And bonus: you're not advertising Claude when you wear it - you're expressing something about yourself.

Image source: https://www.instagram.com/p/DPW0CJQkmAq/

3. The location was *chef’s kiss*

Anthropic didn’t need or want thousands of visitors to their event. Hell, they didn’t need hundreds. They just needed Air Mail’s already dedicated morning coffee collectors, their afternoon dawdlers, their intellectual niche.

And by doing so, Anthropic wore Air Mail’s sophistication and penchant for a slower life like a glove.

It succeeded on vibes and vibes alone - and that, my friend, is a legit marketing strategy.

4. Scarcity, community and FOMO did some heavy lifting

Yep, they ran out of hats.

 Sam McAllister, Anthropic's team member who helped run the event, laughed about it: "We definitely didn't order enough merchandise, that's for sure."

But, Sam, Sam, Sam, was that not just a clever marketing ploy?

Because waiting two hours in line made the hat more valuable than if Claude had just mailed it.

Because the effort became the experience. Your photos, proof.

And even if you left without a hat, you left with a moment and a story to tell others back at your desk.

"You're there to be part of a moment, to say 'I was here,' to share it with others who get it."

Eda Akturk, coder

FOMO, inclusivity, scarcity, community. These are four of the most powerful forces in modern brand marketing, and all were achieved by a branded hat and a good flat white.

Read more: Are Labubus trolling marketers? What B2B brands can learn from the latest TikTok craze

5. Humans win over brand accounts

And here’s one of the most influential parts of this whole pop-up: the hype didn’t come from Claude’s official channels.

Nope.

It came from the infamous Sam, whose casual, chaotic, very all-caps posts increased the energy around the event.

The messages were like something you'd send to a friend, not a press release.

And that’s because people are bored with corporate accounts. They want the faces and the personalities behind the brand.

And when the team behind the product are the one creating the excitement, it’s authentic community-building with longevity in mind.

Read more: How brands survive audience exhaustion, according to our experts

What your brand can learn from the “Thinking Cap”

A lot, it turns out.

1. No logos

Instead of putting your logo on your merch, why not experiment with an idea instead?

When your branded product is connected to a genuine idea that your brand stands for, the more powerful (and wearable) your merch becomes.

2. Everything has a part to play

Where and how you show up physically communicates your values before you say a single word, and a thoughtful, well-chosen activation space says more about your brand than any tagline.

Image source: https://www.trendwatching.com/innovations/anthropics-zero-slop-pop-up-invites-new-yorkers-to-slow-down-and-think

3. Order with scarcity in mind

It might feel counterintuitive, but by ordering with scarcity in mind, you turn your merch into an experience of limited-edition drops, short-run products, and exclusive events. These transform passive audiences into people who feel genuinely lucky to have been there.

4. Let your humans be themselves

Some of the most effective brand content doesn't come from a brand's official account. Give your people permission to share, and then trust them to do so authentically. It’s all about trust.

Read more: How to tell your authentic brand story with merch 

5. You don’t always need a hard sell

Have another look at the “Thinking Cap”. It’s not a "Try Claude Now" cap, is it? Not a “Limited Deal Today with Claude” cap.

There’s no button on that hat. No QR code. No discount code.

And yet: one person waited ninety minutes in line and switched providers based on how the whole thing felt.

That’s Return on Emotion (ROE) in action.

What’s Return on Emotion?

Return on Emotion (ROE) is all about turning every activation into an unforgettable, brand-defining moment fueled by emotional connections and reactions.

Because, did you know, 64% of consumers are more likely to remain loyal to a brand with which they feel an emotional connection? And with 95% of purchase decisions driven by emotion, brands are harnessing these insights to build meaningful connections that inspire loyalty and engagement through emotional bonds.

You can read more about Return on Emotion over at Brand Revolution.

Thinking about merch?

In a noisy, over-marketed, AI-saturated world, the brands people remember are the ones that give them something tangible to experience and something worth talking about.

Anthropic took a digital product and made it physical. They took a brand value ("keep thinking") and made it wearable. They created a space that felt human in an industry that often doesn't, and people responded with their time, their feet, their social posts and, eventually, their loyalty.

The “Thinking Cap” isn't something that’s going to live in a drawer or get dusty on a hook. It’s something that can be worn by everyone - even if they don’t have any knowledge of what Claude and Anthropic are.

That’s the beauty of it: the ones in the know, know, and the ones that don’t still think it’s pretty cool.

The “Thinking Cap” is what promotional merchandise can be when it's rooted in a genuine brand idea - when it becomes a conversation starter, a cultural touchpoint, and a quiet little act of community-building.

ChatGPT could never.

Get in touch with us today to brand something your audience will actually want to wear.

Want to see what you could do with a hat? Check out our full range of branded hats, caps and more headwear essentials below.