Why Microsoft Executive VP Scott Guthrie always wears a red polo shirt

Microsoft
Executive VP Scott Guthrie wearing his signature outfit at
Microsoft Build 2018.
Microsoft

• Microsoft Executive VP Scott Guthrie is known for two
  things: His leadership of Microsoft’s fast-growing cloud
  computing and AI businesses…and his trademark outfit of a red
  polo shirt and jeans. 
• He even got teased for dressing up for an event with
  famed fashion designer Victoria Beckham. 
• He says that the red polo shirt was his good luck charm
  when he was just starting out as an on-stage presenter, and it
  kind of grew into a phenomenon all its own.

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. 

Scott
Guthrie presents on stage at a Microsoft conference in 2008 — one
of the first times he rocked the red polo.
Fred Prouser/Reuters

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.