Battle of the Brand Trip

J.Crew vs. Matteau, a Brief History of Brand Trips, and an American Heritage Brand in Puglia.

On Wednesday I fired off a half-baked thought in the Substack Notes app: “Not being a hater but everything about the J.Crew trip feels wildly embarrassing.” When someone asked me to explain, I had to pause. For those of us who are just joining, (not chronically in brand land) J.Crew took 20 or so influencers (writers, stylists, creators) to Puglia to celebrate their collaboration with Masseria San Domenico. The backdrop was gorgeous, the execution flawless, the fits immaculate. And yet… the vibes looked forced. What’s an American heritage brand doing partnering with a masseria in Puglia, anyway?

If you care about this kind of thing, it’s no secret that J.Crew has been in the throes of an identity crisis since the departure of creative director Jenna Lyons and longtime CEO Mickey Drexler in 2017. (Arguably, it started even earlier but that’s another story.) As Glossy put it at the time: “J.Crew’s mistake has been reacting to a changing market by trying to be everything to everyone, instead of committing to one customer and one clear point of view—when originally, clarity of vision was their strong suit.”

A Brief History

Brand trips exploded in the 2010s, when beauty and fashion brands realized that flying influencers to destinations could deliver more impact than traditional ad campaigns. By the late 2010s, brands like Tarte and Revolve were known less for their products than for the spectacle of their trips. It became formulaic fast. Post-pandemic, the tone shifted. The brand trips that land today feel more curated, and more personal.

Emotional Marketing

At their best, brand trips aren’t selling product. They’re selling sentiment. A world, or a life, you want to inhabit. You don’t win people over with logos carved into fruit or itinerary slideshows dressed up as content. You win them over by creating a mood. Product is often just the access point. The real story is about identity. How it feels to be a part of the world a brand builds.

“In addition to the capsule collection, J. Crew transformed the hotel's beach club into J.Crew A Mare, a one-of-a-kind brand experience bringing the best of J.Crew summer to the Italian coast, so the next morning, we headed straight to the sea — and transformed may be something of an understatement. Upon arrival, it was clear that this was no ordinary beach club and nothing had gone untouched — ashtrays, lifesavers, playing cards, even lemons had been J.Crew-ified, making for an extremely aesthetic — and elevated — beach day”

Lauren McCarthy, Nylon

Matteau Gets It Right: Taste Over Hype

Enter Matteau. Their recent brand trip was a celebration of the brand’s 10-year anniversary, set against the backdrop of the French Riviera: a fitting location for a label known for its quiet luxury. Held at Les Roches Rouges, the trip brought together a small, thoughtful group of women who reflect the brand’s ethos: refined, intelligent, creatively engaged.

Guests included stylists like Brie Welch, editors like Simay Demirel, and creatives such as Diane Louise Bartlett; women who aren’t just aesthetically aligned with Matteau, but who also carry cultural weight in their respective fields. The vibe was intimate and distinctly un-branded: long, languid meals; unposed moments; wardrobe staples worn in the wild.

Instead of the typical influencer fare, the content that emerged felt editorial, lived-in, and personal. You got the sense that the brand trusted its guests to shape the story, not just execute a moodboard.

The content from the Matteau trip was published in real time. The only evidence on their feed is a few polaroids.

When it becomes too literal, too staged, it breaks the spell. You stop feeling transported and start feeling marketed to. That’s the difference between storytelling and a campaign.

Now, contrast that with J.Crew’s trip. Plenty of star power, no shortage of pretty moments but it didn’t add up. The group felt randomly assembled, like fashion week table assignments airlifted into the Tuscan countryside. Don’t mistake me, I’d love to listen to Laura Reilly and Chris Black talk about the NY menswear scene, but I kept searching for a through-line between the super fashion-y people, the europeans (??), and the subway guy that I had to mute on Instagram.

Relevance > Reach

We’ve all seen these trips, the same influencers, over and over, promoting different brands every week. Beautiful, yes. But increasingly disconnected from the products they’re paid to endorse. And consumers can feel that. The algorithm might not notice, but people do.

Today, brand trips aren’t just about reach. They’re about relevance. Cultural fluency. That comes from having a point of view and inviting people who not only wear the clothes, but expand the story around them.