I was raised to dress casually and pragmatically, mostly as a survival technique, since Ohio’s weather varies a lot more than people think. That impulse has been increasingly incongruous with living in New York City for nearly two decades and also with my professional life, which for years now has included fancy events of various kinds, requiring clothing to match, from dinners with Lexus in Japan to concours events in Europe to pretty much any event with Ferrari involved.
Still, outside of these costume changes, I managed to hang on to vestiges of my upbringing, namely Carhartt jackets, jeans, and T-shirts for everyday use. This was the happy state of affairs until recently, when my colleagues decided I needed a makeover, perhaps growing tired of the T-shirt and jeans routine. The Pebble Beach Concours d’Elegance, the most prestigious car show of its type in the world, was also coming up, and I would be attending for the first time, which was the perfect excuse.
Pebble is the kind of event where even the billionaires in attendance try to look their very best, and the car journalists, meanwhile, treat it as prom, an opportunity to show off for each other and pretend, for a minute, that at home they don’t commute in a wretched old Mini. I’d successfully resisted going for many years but decided to make an exception, finally, because my colleague Viju Mathew, Robb Report‘s longtime automotive editor and a Pebble Beach vet, offered to help guide me through the whole experience.
I also wanted to see what the fuss was about, but first, I needed some clothes. For that, another colleague set me up with a fitting session at Eleventy Milano, an Italian fashion brand founded in 2007 with a showroom on Madison Avenue, which graciously offered to loan me outfits. Alex Badia, who is the head of the Fashion Department at WWD, also agreed to help me, taking me through the racks at Eleventy to form two outfits that would see me through the major events at Pebble.
Alex has an intimidating resume, having spent over two decades in fashion, much of that overseeing fashion shoots and stories at WWD and other publications. He’s also been a constant presence at shows and red carpets, including at the Golden Globe Awards. I assumed that he hadn’t had to deal with many like me—a style idiot—very often, talking as he does all the time with industry professionals, but I was wrong.
Justin Festejo
“I have an older brother who is very much like Erik, who doesn’t like clothes so much. They see it as a way of getting dressed, but nothing that expresses feelings or emotions,” Alex said. “We have a lot of work ahead of us.”
Alex had definitive (and good) ideas about what I needed, and so did the experts at Eleventy, who seemed to be familiar with dealing with my type: someone who isn’t opposed to nice garments but may not know much about them.
I ended up with two outfits—but only after rejecting several others. There was a Prince of Wales jacket with lots of personality but was also a little extra for my taste. Alex also showed me a pastel pink blazer that I declared to be too much “beach” and not enough “cars.” He pointed out that the jacket was actually quite on trend, but he agreed we could find something else.
Finally, we landed on the winners. The more casual look he conjured included a navy crop jacket with a touch of brown, which Alex said is a big color for the season. That look included a brown T-shirt, dark blue joggers, and white sneakers. The more formal look relied on a darker blue, shadow print Prince of Wales jacket that Alex said was more subtle than the first alternative (I agreed). A chambray shirt with a “hint of Western,” light khaki pants, and dark brown leather shoes completed the look.
“You can wear the tie, or not,” Alex said. Both outfits were calculated for Northern California weather: chilly in the mornings and sunny, verging on warm, in the afternoons.
At Pebble and a warm-up event called The Quail, A Motorsports Gathering, I wore each outfit and conformed to the milieu so seamlessly that no one raised an eyebrow, which was the goal. I was even confused on a few occasions for a person with a tremendous amount of money. I showed my partner photos from the event, and she said I looked good, but also like a completely different person.
A normal day at the office (left) compared with my new look at Pebble Beach.
Justin Festejo
After a short while, I also forgot what I was wearing and worried more about professional tasks at hand, like gathering information and photographs of the cars on display. I reflected on the nature of clothing and how, truly, it can change perceptions in an instant, and even convince some people that you have some measure of status.
Alex said I looked good, and so did Viju and the rest of my colleagues, who also seemed to harbor a faint hope that this experience would transform my day-to-day style. It did, in a way, prompting me to upgrade many wardrobe staples, and giving me a new appreciation for fit in particular.
It also opened my eyes to just how much thought and care go into styling a single human for just a couple of days: in this case, almost a half-dozen people and many dozens of emails. That is probably a fraction of the attention someone of even minor importance gets—to say nothing of A-list celebrities.
Of course, there are many people who do it all on their own, too, for pure love of the game, and for whom I now have incredible respect. As an everyday matter, I couldn’t justify the time or expense, but at Pebble this year, it was a grand time pretending.
Authors
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Erik Shilling