It's unusual for a tech exec, even a high-powered one, to be chided for dressing too nicely. And yet, that's what happened to Scott Guthrie, the top Microsoft exec in charge of cloud and AI.
In June 2017, he posted a photo to Twitter of himself with famed fashion designer Victoria Beckham, where he was wearing a button-down shirt and slacks, with no tie. This innocuous business casual getup garnered some odd questions about his fashion choices: Where was his famous red polo shirt?
"The awesome thing is when I retweeted the picture on Twitter, no one asks why are you with Victoria Beckham?' Guthrie told Business Insider in an interview at Microsoft headquarters in July. "Everyone just asks, 'why aren't you wearing the red shirt?'"
Indeed, the red polo shirt is a key part of his look. As long ago as 2009, a company event started with a video implying that Guthrie's red polo is as iconic to Microsofties as Steve Jobs' turtleneck is to Apple fans. Just last year, Guthrie ran the "Azure Red Shirt Tour," where he spoke to developers in five cities about the Microsoft Azure cloud.
The origin of the outfit goes back to 2007, when Guthrie was a general manager with Microsoft's developer division, says Guthrie. He had already distinguished himself as the co-creator of ASP.NET and .NET, two of the company's most popular programmers, and was being called on to present publicly at Microsoft events.
He first broke out the red polo shirt for one of those events, where Microsoft introduced all kinds of new things. It went so well, he says, that he decided that the red polo was just lucky. So when he was called on a few months later to do another keynote, he decided, "you know what, I'm going to wear the same lucky shirt," he says.
"It started off as a lucky shirt, and now it's become a thing of its own," says Guthrie.
Indeed, Guthrie says that the response to his photo with Beckham isn't atypical. If he doesn't wear the shirt, he's met with waves of disapproval from Microsoft fans.
"Now if I don't wear a red polo and I do a talk, I got hundreds of Twitter comments," says Guthrie "Why am I not wearing the red polo?" It's to the point where wearing the shirt is almost an obligation, he says: "So now I feel like I have to."
As a funny postscript, Guthrie recalls that one of his first times wearing the red shirt was in a demo to Netflix circa 2007, where it settled on using Microsoft's Silverlight technology to power movie streaming in the web browser. He remembers going to Blockbuster to ask execs about their streaming media strategy, not long after only to be met with shrugs.
"It's amazing how things have turned out," says Guthrie.
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