Here's how Brunello Cucinelli (and his $5,000 blazers) became Silicon Valley billionaires' favorite designer

Brunello Cucinelli, chairman and chief executive officer of Brunello Cucinelli SpA, poses for a photograph inside the company's showrooms in New York.
Christopher Goodney | Bloomberg | Getty Images

For many years, the phrases "Silicon Valley" and "luxury fashion" were rarely uttered in the same breath. Tech industry chic is often thought of as a crisp new hoodie to match a pair of new Allbirds sneakers.

But the worlds of tech and high-end fashion have become more closely linked in recent years, especially after a group of Silicon Valley luminaries made headlines this week for their visit to luxury designer Brunello Cucinelli's Italian headquarters that reportedly included much talk of entrepreneurship and philosophy — and a very unfortunate example of photoshopped diversity.

As GQ magazine writes in an article this week covering that visit between Cucinelli and such tech leaders as Amazon's Jeff Bezos, LinkedIn cofounder Reid Hoffman and former Twitter CEO Dick Costolo, the Italian designer "has become something of a tech-world icon."

While some of the group of tech executives seems to have been drawn to Cucinelli's headquarters to discuss common interests beyond fashion — including running a business, as the designer launched his namesake company in 1978 — it's also clear that the designer's influence has rubbed off on more than one Silicon Valley leader's fashion choices in recent years.

Facebook CEO Mark Zuckerberg at the F8 Developer Conference in 2017.
David Paul Morris | Bloomberg via Getty Images

For example, while Mark Zuckerberg is one of the Silicon Valley leaders most associated with a casual look that's often incorporated a seemingly endless supply of hoodies and flip-flops, the Facebook CEO's signature gray t-shirts are actually custom-ordered from Cucinelli's fashion house, and they cost almost $300 apiece.

Salesforce founder and CEO Marc Benioff is another devotee of Cucinelli's designs. The billionaire CEO reportedly met and Cucinelli in San Francisco four years ago and the two men bonded over the designer's belief in the philosophy of "humanistic capitalism," the idea that business should be ethical and that employees should have a healthy work-life balance.

Salesforce's Benioff: 'Massive' digital transformation driving our growth
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Cucinelli went on to become a regular guest at Dreamforce, the annual conference for Benioff's company in San Francisco, where the designer spoke about humanism in tech in a 2017 keynote speech that included a "fireside chat" with Benioff. For that chat, the Salesforce CEO even reportedly took the stage wearing a pin-striped navy Cucinelli suit made of the rare, super-soft, and extremely expensive, wool sourced from South American animals called vicunas. (Cucinelli's website does not currently list any vicuna items for sale, but a vicuna jacket made by Loro Piana, a similar Italian luxury designer, sells for over $18,500.)

Salesforce CEO Marc Benioff points inside his Brunello Cucinelli suit at Dreamforce 2017.
Michael Short | Bloomberg via Getty Images

It was also at Dreamforce that Cucinelli first met Amazon's Bezos last year, according to GQ. Bezos' own fashion sense seems to have evolved in recent years, with GQ noting that the Amazon founder had already been seen wearing Cucinelli's deconstructed blazers (which can cost anywhere from nearly $2,500 to over $5,000 apiece) before he met the designer.

Speaking about his meeting with Bezos on a recent conference call discussing his brand's quarterly earnings with analysts, Cucinelli reportedly said he and the Amazon CEO spoke for two hours at Dreamforce last year. "He asked me for [wardrobe] advice," Cucinelli said, according to Women's Wear Daily.

So, aside from a common interest in business philosophy, why are Cucinelli's luxury designs such hot-ticket items in a Silicon Valley world known more for its extremely casual approach to fashion? Well, for one, the area's tastes seem to be evolving as denizens of the tech industry mature from dorm-room startup chic to pricier apparel more befitting the current landscape of post-IPO millionaires and billionaires. According to Robb Report, today's Silicon Valley wardrobe staples include more luxury items made by brands like Loro Piana, French fashion house Lanvin (whose $500 sneakers are worn by Microsoft CEO Satya Nadella) and, of course, Cucinelli.

Amazon CEO Jeff Bezos.
Phillip Faraone | Getty Images

Of course, it also helps that Cucinelli's designs tend to feature a blend of high-end luxury and a casual aesthetic that is right at home in Silicon Valley, where even wealthy tech executives and investors are commonly seen sporting fleece vests, jeans and sneakers in board meetings. In addition to the unassuming and plain Cucinelli t-shirts favored by the likes of Zuckerberg, the designer also sells high-end casual clothing like $2,500 sweatpants (made of a mix of cashmere and French terry cotton) and $800 sneakers made from calfskin and washed suede.

These types of items seem to align with the "simple,classic comfortable style" that Victoria Hitchcock, a San Francisco-based fashion stylist who mostly serves clients from the tech industry, says most of her clients come to her to find. Indeed, Hitchcock tells CNBC Make It that Cucinelli has become more popular with tech workers in general (and not just CEOs) in San Francisco and Silicon Valley in recent years even despite the brand's "luxury price point," because of the designer's "approachable casual style."

Cucinelli's designs have gained popularity among the tech set, Hitchcock says, because it is "a strong brand that provides meticulously tailored, five pocket pants and my favorite deconstructed blazers." One of the most crowd-pleasing Cucinelli items, she says, is a travel blazer made with silk and wool that retails for nearly $2,500.

"This is my absolute favorite [Brunello Cucinelli] item ever," Hitchcock tells CNBC Make It. "I can't tell you how many of my clients over the last five years have ended up buying seconds and thirds."

While a blazer that costs thousands of dollars — partially due to the fact they are hand-stitched in Italy and made with high-quality materials like fine cashmere sourced from Hircus goats — is a lot more expensive than the once-standard Silicon Valley hoodie, part of the draw of Cucinelli's jackets is also, simply, name appeal.

On the subject of Cucinelli's blazers, GQ's Samuel Hine writes: "In the fashion world, the Cucinelli blazer is an in-group wink, a sign that you have reached the pinnacle of taste."

Don't Miss: How Allbirds went from Silicon Valley fashion staple to a $1.4 billion sneaker start-up

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