It can be argued either way that we have progressed or regressed when it comes to how people dress at work.  Before I delve into this, let’s discuss a key overriding factor to all of this.  Regardless of how one dresses, it’s your work output and quality that counts the most.  Someone can be a snappy dresser and be an utterly inferior worker with a lack of work ethic.  The smartest guys I’ve come across in the I.T. world tend not to be the most formal dressers and it makes no difference since they’re creating software code to make the world an easier place to live and work in.

My criterion boils down to this – if you see clients you should dress well.  If you’re in Sales or upper management or any other position that requires you to meet your customer base (or potential customer base), you should dress as though you care.  Also, formal settings like a courtroom dictate that professions like lawyers should respect the environment they are in.  Holding a public office should also mandate that you dress well when you are in session.  If you are a consultant/contractor and are working in your client’s office, you should always dress at least in business casual attire since you are representing another company unless the client specifically says you can dress more casual.

For most of us in the I.T. world we never see clients so it truly is OK to wear jeans and a nice shirt if that helps you to a more productive day.  I’ve been in companies where I had to wear a tie and I’ve been in places where a Marvin the Martian t-shirt is considered dress-up attire if it’s been washed.  As long as your jeans didn’t have holes where your underwear was showing, it was considered acceptable dress. 

This is where I think some people can abuse the system.  Unless you live in southern California or Florida or Bermuda, I think shorts, t-shirts and/or sandals are inappropriate.  I don’t mind tennis shoes but I also rarely ever wear mine to work.  Back when I worked in Chicago and wore jeans on casual Fridays, I always felt underdressed on the bus or El train.  Unlike the current city I live in, the rich and poor and middle class all use public transit.  During rush hour in Chicago, I was always surrounded by people in suits and other formal work attire.

Even in our relaxed work atmosphere, you’ll see me in khakis or jeans with a polo shirt in the warm months or a long sleeved, ironed collared shirt in the winter months.  On a rare occasion I might “get crazy” and wear a nice sweatshirt on a Friday. 

I don’t begrudge anyone who dresses uber-casual at work but I feel guilty if I do.  I finally succumbed to wearing jeans on a regular basis as of late.  I figured I might as well take advantage of it in case my next job, whenever and wherever that might be, would be more formal again.  Even with the jeans I still wear nice shoes though. 

As expected, guys are always the schlubbier dressers when it comes to casual wear.  Most women at least have a sense of fashion in the casual department, whereas most guys will wear the bare minimum it takes to be technically “dressed for public appearance”.  Bonus points are handed to those whose shirts aren’t completely wrinkled as though it were either a) hanging out in the dirty clothes hamper or b) hanging out in a pile of other clean clothes on the floor for a week.

For those of you who work at home and can sit around in your undies, I envy you.