The topic of what to wear to work should be straightforward.  Just follow your company’s dress code as laid out in the employee handbook, and there won’t be any problems.  Unfortunately, as many of you probably know firsthand, it is almost never that simple.

The Point of Your Business Wardrobe

This subject is tricky for two reasons.  First, the dress guidelines provided by Human Resource departments are rarely cut-and-dry and leave a lot of grey area for interpretation.  Second, the real objective of your business clothing is not merely to avoid a slap on the wrist from HR, but to convey your attitude about life and work to co-workers and supervisors.

Specific dress codes vary so much by company that it’s best only to offer general advice.  My experience with these guidelines has been that on any point that is unclear, it is always best and safest to follow the most conservative interpretation of the rule as possible.  

For example, you might wonder if it’s appropriate to wear your Jordan Spieth polo and khaki shorts combo on the day of the company golf outing. If you’re unsure, it’s probably best to err on the safe side and wear your normal clothes.  

The worst case scenario is that you find out later that the golf outfit would have been acceptable, and are delayed five minutes on the way to the course to change.  This “play-it-safe” approach works best, regardless of the situation, be it type of pants, shirts with or without a collar, skirt length, necessity of ties, long sleeves vs short, etc.  If you are still unsure about something, one can always ask the HR department if it would be appropriate before wearing it into the office.

An Outward Display of Your Inner State

Once you’ve covered the basics, it’s important to consider the kind of message you are sending with your clothing choices.  I’m not referring to fashion sense, but to a general reflection of your approach to life and to work.

Many companies have broadly defined dress codes that allow for a wide range of acceptable clothing choices.  In my experience, most employees will congregate around the lowest allowable level of such guidelines, preferring comfort and convenience over a groomed appearance.  I once worked for a company that relaxed its dress code for what was intended to be a short period of time during a storage clean-up project. After the project ended, HR gave up ground permanently as employees continued to wear jeans and tennis shoes.

I’m not sure why so many people opt for the least dressed-up option allowable under their company’s rules.  It may be that they are oblivious to the message they are sending. However, I think in most cases, they simply do not care.  To them, the slight advantage in convenience and comfort is enough to offset any signals of laziness or carelessness they may be expressing via their clothes.  

This is a bad way to think about it.  It is such a simple thing to do right, but I am continually surprised by how many people miss the mark.  Nothing says “I’ve given up,” quite like a wrinkled, untucked polo shirt and blue jeans.

The good thing about business dress is that a very small effort will instantly put you a class above the majority of your peers.  You don’t have to wear tailored business suits or expensive Swiss watches.  Simply being well-kempt and presentable is a great start.

Find What Is Appropriate

It can sometimes be difficult to determine how well-dressed you should be, because it is possible to over-do your wardrobe.  For example, if polo shirts and slacks are the standard in your workplace and you start showing up in a full suit everyday, people may think of you as aloof and elitist. They may also wonder if you are actively looking for another job.  

The appropriate level of dressiness will vary significantly from office to office, region to region, and country to country.  A good rule of thumb is to observe how the best-dressed folks in your office look on a daily basis, then dress at this level or slightly better.  This way, you will be the best dresser in your workplace, but you won’t appear egotistical or standoffish.

I know what some of you are thinking right now.  The way you dress shouldn’t matter.  As long as you aren’t violating any company policies, the only thing that should count is your work performance.  It should not matter whether you do your work in jeans and a polo or in a full suit.  Maybe in a completely just world, that would be true.  But in this world, the way you present yourself matters.  The way you present yourself influences your boss’s opinion of you, even if only subconsciously.

“But what about Mark Zuckerberg?  Elon Musk?!? Mark Cuban??  They are some of the most successful business-people of all time, and they wear t-shirts!”

You got me there.  None of the entrepreneurs mentioned above put much effort into the way they dress, so let me make an exception.

Once you have founded a billion-dollar company or three, feel free to wear whatever you want to work and I won’t say anything.

At this point, your livelihood will no longer depend on a middle-manager’s opinion of you.  Until then, take care of how you dress and present yourself.