Business casual -- two words to create an overwhelming sense of dread in any executive.
Once upon a time, dressing for work was easy. Everyone chose smart. Then business casual started to appear on dress codes and the simple decision of what to wear to work became incredibly complicated.
The internet tells me there is no generally agreed definition of 'business casual'. It seems formal suits and ties are too much for men, but they should wear smart trousers and a collar. Women, on the other hand, should focus on trousers and a knee-length skirt, and a blouse or shirt with a collar.
But those simple guidelines mask subtle variations by company and event. As a female CIO said to me recently: "Are smart jeans OK? What about flats? The term 'business casual' is the very definition of an oxymoron."
So, who should we blame for this? Probably the person 20 years ago who thought it was a good idea to give people the opportunity to 'dress down' or 'go casual' on Fridays. And as the years passed, and as traditional blue-chips desired the hipster chic of their startup counterparts, casual Friday became dress-down every day.
In fact, companies are now so eager to keep talent happy that the unthinkable becomes thinkable. Investment bank Goldman Sachs -- which is known for its strict rules on what workers can wear -- sent software developers and engineering staff a memo recently telling them they can dress casually, but they might think about smartening up to meet clients.
That blurring of responsibilities and settings is where the problems with business casual really become acute.
Get business casual wrong and you can incur the wrath of the very people who have relaxed the rules. As one CIO said to me, relaxed dress codes in more formal businesses can lead to wide personal interpretations, with people often stepping beyond what senior management consider to be "acceptable".
The confusion around working attire is not just confined to software developers and engineering staff. Everyone in the technology team is affected by the business casual conundrum, including IT leaders and the people they interact with.
I went to interview a CIO recently who was dressed in jeans and a t-shirt. I turned up in trousers and a shirt. I was the only person in the IT department with a collar.
I felt like the overdressed work experience boy who is desperate to create a good impression, and failing badly.
Thinking I had learnt a valuable lesson, I switched my approach around for my next meeting with an IT leader, turning up in jeans and trainers. The CIO I was meeting was inevitably in a suit.
We walked through the office together -- a middle-aged man with his impossibly middle-aged and inappropriately-dressed son. It was, in short, a hideous experience.
My dress sense neurosis has become so serious now that I have started thinking of phoning ahead to ask CIOs how they would like me to dress. But if it is bad for me, it must be hellish for technology chiefs.
Inside their departments, IT leaders need to dress down to feel attuned with the talented coders they have fought so hard to attract. Unfortunately, dressing to impress the hipster generation is likely to backfire as badly as a parent trying to impress their teenage son or daughter's friends.
The challenge is no easier outside the IT department. Experts queue up to tell CIOs they need to spend most of their time engaging with people around the rest of the organisation.
Now imagine the outward-facing CIO roaming line-of-business departments in a band t-shirt and skinny-fit jeans.
CIOs already moan they are not taken seriously enough by the rest of the business. If something goes wrong with the projector in a board room meeting, other executives will always turn to the IT expert. Dressing like a student is unlikely to improve the situation.
IT leaders must also consider attire for external work. Modern CIOs engage with an ecosystem of partners, from non-competitive firms to vendor partners and onto fleet-of-foot start-ups. Then there are evening events, most of which take place in smart venues with formal dress codes. Now think of that broad range of organisations and venues, and try and think of a single dress code that works across all situations - you can't because there isn't one.
It is common for executives to have a footwear alternative or a tie close at-hand in case of changing business circumstances. However, the dress code challenge has reached such a critical stage that many CIOs are probably thinking of getting a wardrobe fitted.
I'm sure the problem of dress codes affects other lines-of-business, too. However, the issue seems particularly acute in the IT department. I've been to digital marketing conferences, for example, and everyone dresses casually. The technology conference remains a bewildering mix of suits and hipsters. No one knows how to dress in IT anymore. No one.
To quote one CIO who I chatted with recently: "So much time is wasted spent on debating dress code, you really have to question the value that it provides. In the end, it comes back to empowerment, people value being able to decide what they want to wear for themselves."
I guess the moral of the story is the same as it ever was: CIOs should dress appropriately for every business situation. The problem, however, is that the rules for every situation have become muddied and unclear. Thanks for nothing, business casual.