Monterey Car Week is one of those events that is difficult to understand until you’re there. For several days in August, the Monterey Peninsula becomes a gathering place for collectors, car enthusiasts, designers, brands, and, increasingly, the fashion crowd. There are auctions in converted hangars, private houses in Carmel, dinners overlooking the water, and cars—lots of them—parked everywhere from hotel driveways to the lawns of Pebble Beach. The week’s schedule can feel relentless, but that’s also part of the appeal. You can spend the morning looking at a 1960s Jaguar, the afternoon test-driving a new Defender off-road, and the evening eating dinner with a group of people who have flown in from around the world to talk about cars.

Coming from fashion, I found the week surprisingly familiar. The conversations around cars often sound a lot like the ones we have around clothes: What’s the history? Who designed it? What makes this version different? Is the original better? There’s also the same fixation on materials, color, proportion, and craftsmanship. The difference is scale and the fact that you’re expected to know your chassis numbers here. I didn’t. But I did find myself paying attention to the details I would normally notice in a showroom or on a runway: the color of the leather, the finish of the paint, the shape of a seat, the way an old car had aged. Monterey made a convincing case that fashion and automotive design share more than just a well-dressed audience. Both are industries where design is a way of communicating taste.

Sotheby’s Monterey Auction Preview

The first stop was the Sotheby’s Monterey auction preview, where the cars were arranged almost like an exhibition. Even without knowing the market value of every lot, it was easy to understand why certain cars attracted a crowd. The provenance, condition, and originality of each one seemed to invite the same kind of close inspection you might give a rare vintage garment. One of the highlights was the reveal of a Range Rover Classic auction car, presented alongside its contemporary counterpart. Seeing the two together made the evolution of the Range Rover design especially apparent—what has changed over the decades and, more interestingly, what hasn’t. The Classic still looked unmistakably like a Range Rover, just stripped down to a much simpler version of the idea.

The Range Rover House

Range Rover House in Carmel-by-the-Sea was a different kind of experience. Rather than focusing solely on the vehicles, Range Rover created an environment around them, with new and vintage models placed throughout the property alongside spaces for commissioning a custom car, food, and wellness. There was wood-fired pizza, Augustinus Bader treatments, and plenty of space to sit outside and take in the California weather. The most talked-about moment was the reveal of the new Range Rover SV Pearl Luster, a one-off car designed around the soft, iridescent quality of a pearl. The car was finished in a bespoke white pearl exterior with an interior that incorporated orchid-colored leather and mother-of-pearl details. It was a good example of where the luxury-car market is heading. Increasingly, the point isn’t just choosing a model. It’s deciding exactly how you want it to look.

The Quail

The Quail has a slightly different energy. It’s polished but less formal, with a mix of vintage cars, new launches, food, and brand activations spread across the grounds. The cars are obviously the main attraction, but the event is also very much about the lifestyle surrounding them. You can stop for lunch, look at a rare Ferrari, walk into a new brand installation, and then find yourself talking to someone about what they drove there. I was most interested in the contrast between the older cars and the new ones. Put next to each other, you could see how much automotive design has changed and how often contemporary designers return to the same shapes and references.

Land Rover Experience

A driver took me off-roading in the new Defender, then got behind the wheel of a ’90s Defender. The newer car was impressively easy to drive over terrain that I would have otherwise avoided entirely. The older Defender was another story. It required considerably more attention and felt much more mechanical, which made the comparison useful. Driving the two back-to-back was a reminder that nostalgia can make an older design look deceptively simple. The modern version may be more refined, but the basic idea is still there.

Preview of Concours d’Elegance

Ahead of the Concours d’Elegance, I got a first look at several of Jaguar’s historic cars, including cars associated with Steve McQueen, Princess Diana, and the British royal family. Seeing them in person was different from seeing the same cars in archival photographs. The details that become part of the story—the particular color, the interior, even the modifications made for a specific owner—were suddenly tangible. The cars also offered an interesting look at how personal taste is attached to an object. McQueen’s Jaguar XKSS is recognizable partly because of its association with him, but Princess Diana’s XJS has a different kind of cultural history. In both cases, the car became part of the person’s public image.