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What It’s Like to Dress Silicon Valley’s Elite

There’s more to the Bay than sweatshirts

(josephrosenfeld.com)
(josephrosenfeld.com)

Silicon Valley has long been known for its casual style; it’s the type of place where a company’s engineers can walk around in Tevas and fleece and still appear more formally dressed than its CEO. But in the past decade, as a new class of Ivy League–educated entrepreneurs has flooded Northern California, tech workers have developed a taste for high fashion. Yes, big names like Y Combinator’s Sam Altman still get turned away from the Ritz for wearing sneakers — but that’s happening at the same time that almost every major tech CEO, from Snapchat’s Evan Spiegel to Yahoo’s Marissa Mayer, has been dolled up and splayed across the pages of Vogue. At least one invitation-only dating network sends its clients to a stylist for a complete overhaul before they are allowed to begin dating. Valley Fair, a shopping mall in San Jose that has long been the center for retail in the South Bay, has quietly accumulated a cadre of luxury retailers that could rival any Beverly Hills block, the most recent of which include David Yurman, Miu Miu, and Prada boutiques.

“All these brands are there now not just because Silicon Valley has a bevy of high-income earners,” says Joseph Rosenfeld, a self-proclaimed “brand strategist” who is more intimately familiar with what he calls the area’s “luxification” than most. “The reason that this is happening is because the high-income earners who are here are finally getting on board with doing something in terms of developing their style.”

Rosenfeld has been dressing people for the past 27 years, and now he’s riding this wave. The 47-year-old native Chicagoan got his start as a personal shopper after graduating college, working at Neiman Marcus. But when he moved to Silicon Valley, he became fixated on what he recognized as a very creative and ambitious population of clients — namely CEOs, lawyers, product managers, VCs, engineers, scientists, and graphic designers at major companies like Apple and Google.

“It occurred to me that a lot of people in high tech truly could benefit from my expertise,” he told me when I visited his modern San Jose studio/office this week, dressed impeccably in subtle patterned slacks, a dark blue sweater, and shiny loafers. “I did not want to strictly become the guy who was really great at dressing socialites and wealthy retired men. I really wanted to add value to working people.”

It’s no coincidence that Rosenfeld runs his business much like any other detail-obsessed technologist in the area. His show room, a well-lit minimalist white space, feels a bit like an Apple store — except with carefully put-together ensembles in place of gadgets. Rosenfeld’s approach to dressing clients is holistic: His contracts last an entire year and are separated into “capsules” — collections of clothing based on season or occasion. He doesn’t make his fees public, but he makes selections for clients based on their income levels. His bookshelf is stacked with art tomes and meditations on the professional self, ranging from the Metropolitan Museum’s limited edition Fashion in the Age of Technology, to kitschy collector’s items like The Official Silicon Valley Guy Handbook. These books and his frequent trips to fashion shows in New York are what Rosenfeld says have helped him remain a “thought leader about what is possible for all of us stylistically.” The long dining room on the lower floor of his apartment doubles as a conference room where he is working out the details of his very own startup, an app that translates his proprietary personality-evaluation and color-profile techniques into an algorithm for shoppers.

(<em>Alyssa Bereznak)</em>
(Alyssa Bereznak)

Though Rosenfeld has encountered practically every fashion faux pas possible — ranging from outdated executive suits to practically threadbare basics — he does not outwardly decry typical Silicon Valley staples like the ubiquitous hoodie. Rather, he argues that the culture of tech companies to maintain an overly-casual dress code can sometimes wash out individuality.

“One of the failings of the democratized, wick-away-sweat workout T-shirt with mom jeans and huge oversized sneakers — all worn by people for the sake of comfort or even for the sake of invisibility — is it’s a disservice to most individuals,” he said. “It might appear to be sort of classic but that type of messaging doesn’t necessarily make a person appear to be with it. And these types of things really matter in high tech.”

Individuality is Rosenfeld’s highest priority. Over the course of getting to know clients, he often pushes them to define who they want to be, a deeply intimate process that has, at times, touched him to the point of tears. He recalled one “deeply introverted” client who had sold his startup to Google and become an early employee there. He told Rosenfeld that each day, he came home from work and held a stuffed animal.

“I have to give him clothes that are so squishy-gushy, tacitly soft because he knows he can’t actually wear flannel pajamas to work,” Rosenfeld said. “He would really love to feel as though he were enveloped in a very comfortable bed with his own stuffed animal. But he has to be his own stuffed animal all day long.”

With other tech employees, Rosenfeld cites obsessively designed electronics as a motivation to remain more vigilant to maintaining a unique personal style.

<em>(Alyssa Bereznak)</em>
(Alyssa Bereznak)

“I use the iPhone as an example for clients,” he said, gesturing to mine. “The elegance of the iPhone, the simplicity and the boldness of it, the overall aesthetic, the way it works and functions and supports the ways we all want to live our lives. I say, that really matters to you, but the way you design you should matter the same way.”

After helping hundreds of clients over the years, Rosenfeld says he is finally seeing technologists appreciate the value of a sharp wardrobe — as a method to remain competitive and confident in a highly skilled workforce and, in some cases, to improve their chances to earn VC funding.

“I don’t want to paint a picture that all of a sudden, everyone’s wearing Prada sneakers and YSL bags,” he said. “That’s definitely not happening. But what I’m seeing is that there is a time and a place for the REI fleece zip-up and there’s a time and a place to carry a Ferragamo bag.”

Rosenfeld has seen the cold, hard proof to believe it. Earlier this year, a client came to him with a very Silicon Valley problem. He was an inventor with dozens of patents who would soon be giving a keynote presentation on a processor he cocreated. And he had nothing to wear.

Luckily, this inventor had already completed Rosenfeld’s extensive onboarding process — checking off a list of aspirational personality traits, creating a color profile, and a What Not to Wear–esque closet makeover — and the foundation for the task was set. It was only after Rosenfeld previewed a few slides from the keynote and noticed the company logo that he knew what exactly to do.

“That tipped me off,” he said. “I thought: Well he has that color in his color palette.” The outfit was a hit: During the presentation, the speaker onstage complimented the inventor’s tie.

“In the high tech world, people don’t often make a big deal out these things, and yet they couldn’t ignore how fantastic he looked.”