The Style Guru Transforming Techies From Frumpy to Fashionable - OZY | A Modern Media Company

The Style Guru Transforming Techies From Frumpy to Fashionable

The Style Guru Transforming Techies From Frumpy to Fashionable

By Sean Culligan and Leslie Nguyen-Okwu


Because hoodies and sneakers are on their way out.

By Sean Culligan and Leslie Nguyen-Okwu

Something is missing from the Giorgio Armani store in San Jose, and it’s not just the price tags. Sandwiched between Versace, Balenciaga and other tongue-twisting fashion linchpins, this tony boutique sports the sleek minimalism of an Apple store. But then Joseph Rosenfeld saunters in, peppy as a cheerleader. All is now right.

Today at the high-watt luxury section of the Valley Fair Mall, the 47-year-old fashionista is easy to spot: bright blue socks, figure-hugging McQueen slacks and, as a final touch, an embroidered pink daffodil on a Dolce & Gabbana jean jacket. High fashion and high tech don’t usually go together, but Rosenfeld quietly sits at the intersection of these two worlds. He may not exactly be a brand name in Milan or Paris, but he’s transformed dozens of Bay Area techies from frumpy to fashionable through his What Not to Wear–like makeover, the “sticker shock” fees of which run in the thousands. His high-wattage Rolodex of clients includes high-powered tech attorneys, graphic designers from Apple, senior engineers at Google, uber-rich venture capitalists at the prominent firms along Sand Hill Road, wives of tech billionaires, etc. He gets a little clammed up when it comes to actually name-dropping clients, but some call him the “image maestro” of Silicon Valley, says former client Zile Rehman, the longtime IT guy at Nyansa, a software company in Palo Alto. Rosenfeld took him “out of my fashion doldrums.”

Two years ago, Silicon Valley held its first cutting-edge Fashion Week, with 3-D printed garb, gadget couture and drones flying down the runway.

Others praise Rosenfeld for his discreetness — which is perhaps why none of those aforementioned tech celebs responded to our requests for comment. His makeovers are extensive for each client, spanning all four seasons. From spring to winter, Rosenfeld scours clothing racks — not runways — from San Francisco to London, adorning his nerdy, shop-a-phobe startuppers with cashmere hoodies, Lanvin sneakers and Gucci loafers that turn up the glitz but still suit the laid-back Valley ethos. “It’s not about the clothes; it’s about the powerful image that you portray,” Rosenfeld says, adjusting the thick black frames that overwhelm his thin face.


People like Rosenfeld comprise part of the increasingly large posse of image consultants and coaches that tech execs now sport. According to TrackMaven, 39 percent of CEOs used an executive coach in the last 12 months, a proportion that increased dramatically as their companies grew to scale. Between 2009 and 2014, the personal-shopping industry grew more than 4 percent to $762 million and more than 28,000 personal shoppers in the U.S., according to research company IBISWorld

After all, “the most fashionable accessory of all time was invented in Cupertino, more than whatever you got out of Prada or Gucci,” says Chris Lindland of Silicon Valley Fashion Week, referring to the iPhone. The craze is, indeed, building: LA-based Snapchat’s Evan Spiegel and Yahoo’s Marissa Mayer both graced the glossy pages of Vogue between 2013 and 2015. Square CEO Jack Dorsey regularly sports Hermès suits while Facebook COO Sheryl Sandberg opts for Prada ankle boots. Two years ago, Silicon Valley held its first cutting-edge Fashion Week, with 3-D printed garb, gadget couture and drones flying down the runway. A year later, the fashion event of the year, the Met Gala in New York, chose the theme Manus x Machina; celebrities graced the red carpet in fake steel, glitter and techno-inspired regalia. But here, Rosenfeld is not pulling high-concept garb for his clients. He balances practicality with precision, taking his clients’ eyebrow color and even freckles into account when curating a new wardrobe or color palette. 

The matter-of-factness emerges in Rosenfeld’s telling of his personal story too, though it’s riddled with darkness. Rosenfeld grew up in Chicago with deeply seated insecurities, stemming, he says, from a childhood rape by his female babysitter and the untimely death of his father. His adolescence, he says, was marked by a “pre-suicidal” state (“Because I never had the guts to actually do it”) and no friends (“People treated me like I had the plague”). While we can’t confirm all the details, Rosenfeld speaks openly about this, not just with me; the story is told in his new book. But Rosenfeld’s self-esteem picked up when he grabbed a 1985 copy of The Official Preppy Handbook, which taught him the basics of style, fashion and the golden rule: never wear white after Labor Day. After dropping out of both Drake and DePaul University, he worked as a sales associate at Neiman Marcus and Bigsby & Kruthers before, in true Valley fashion, starting his own venture in 2001 — a style consulting firm in San Jose.

However, his firm is still at odds with the long-standing dogma in Silicon Valley: minimalism. Go little, or go to New York. Jobs’ black turtlenecks; Zuckerberg’s gray hoodie. Dressing to impress means dressing down with jeans and sometimes ill-fitting, untucked shirts, says fashion expert Tosha Clemens. There’s no software update for that. Back at Armani, the sleek-suited cashier tells me Rosenfeld is a regular. Rosenfeld eyes a few soft, handwoven sweaters, like he’s admiring the Mona Lisa at the Louvre. He feels right at home amid the mannequins and crammed racks of tailored blazers and trim trousers. You wouldn’t be caught dead wearing a hoodie here.

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