We've all come to know the tech guy "look": relaxed, informal, yet iconographic. Steve Jobs had his turtlenecks, Mark Zuckerberg has his zipdown hoodies. The strange thing is that many of these guys could literally wear a new suit from a Savile Row tailor every single day, throw it out after one use, and it wouldn't make a dent in their finances. But they don't.

"I wear a pair of jeans and a black t-shirt almost everyday," Erik Schnakenberg, co-founder of Buck Mason, a start-up that sells classic American staples for men, told Marketplace. "It's one less thing to think about." Schnakenberg also adheres to the idea of a man wearing a uniform, much like Zuckerberg and the disheveled Silicon Valley lot. It's important to point out, though, that none of these men are also responsible for helping run the country.

But now, with news that the White House – where the Leader of the Free World both works and resides – will let the U.S. Digital Services team eschew suits for short-sleeves, untucked shirts, and "rumpled khakis," we're at the point where we have to ask just how casual we, as a society, want to dress for work. Is every day becoming Casual Friday

Hawaii first instituted "Aloha Friday" in 1966 as a way to kick start the declining (now handsomely back in style) Aloha shirt market on the island. By the 1990s, in an attempt to create a more relaxed environment, the Hawaiian idea evolved into more American offices granting "Casual Fridays," as employees began shedding grey flannel suits and wearing khakis and polo shirts to their cubicles more often during the workweek. For one day a week, some workplaces allowed jeans and t-shirts in lieu of slacks and ties. 

Things have changed since the Clinton era. Offices are more tolerant of employees leaving the ties and sport coats at home nearly every other day of the week. Mikey Dickerson, admin of the U.S. Digital Services team that's spearheading Healthcare.gov, said he's at least made some concessions. He's willing to wear collars and buttons, and he even donned a suit and tie for a meeting with President Obama, who said it made the team look "more official."

"This is literally only because you're here, Mr. President," Dickerson responded.

We get that a dress code is an old school concept that doesn't necessarily work for a new generation, and that people are individuals who want to express themselves through their appearance and want to be comfortable in stressful situations. Go to an office in Brooklyn, San Francisco, Seattle, or Austin, and you're likely to see people working behind laptops, sitting on yoga balls, and wearing T-shirts, flip-flops, and cutoff denim shorts in meetings with clients. It might not be the norm everywhere, but if it's happening more in the big cities, and if the West Wing – which sets the standard for the country – is now accepting wrinkled slacks and button-up shirts, how much more casual will the rest of us become?

And is it a bad thing if the answer is "more"?