How to Navigate A Casual Dress Code

In my first office job, women were required to wear skirts or dresses, preferably with high heels.  No pants allowed, hosiery mandatory, flats frowned upon.  Yes, I wore oversized blazers that had shoulder pads augmented by shoulder pads, with shiny blouses and long skirts. On my break, I switched my tasteful pumps for Reebok high tops for a quick power walk.  I will also confess, just between friends, to a big floppy bow tying back my poufy hair.  See that outfit on the left?  I had one almost exactly like it. 

Many years later (and I think you can do the math based on the outfit), I sit at my desk in jeans, a t-shirt, a sweater and boots.  My feet don’t hurt, there are no pantyhose to run (back in those days, I always kept an extra pair in my desk for emergencies), and I don’t have dry cleaning bills to worry about.  I think I look OK.  Although I am dressed casually, my outfit is color-coordinated and (I hope) stylish.  And, actually, I don’t wear jeans that often in the office.  I’m more likely to be in slacks, the occasional dress or skirt, and even a blazer once in a blue moon (sans shoulder pads, of course). 

The benefit of a casual dress code is that I get to choose, within reason, how I express myself, my style, and my attitude toward work.  It also serves as an indication to employees that they are valued as individuals, and that the company is more interested in results than formalities.  The casual approach also lowers the barriers between management and staff, encouraging better communication and collaboration.  And of course, t-shirts are less expensive than suits and dresses, not to mention those dry cleaning bills.

As more companies embrace mobility, remote work, and open office spaces, strictly proscribing how employees dress just doesn’t make sense.  However, the sad, but valid, downside to a flexible dress code is that it’s so open to interpretation.  It’s an age old truism (that I’m coining right this very minute) that not everyone’s judgement can be trusted on this topic.  We all think we have good taste, but, to be blunt:  we don’t.  So employers will likely find that they are forced to outline what is allowed and what is unacceptable.

It can be frustrating for management, especially HR.  It’s tough to define what business casual entails, and even harder to enforce.  When one person comes in every day wearing sneakers, even though they’re expressly forbidden by the dress code, is that a battle worth fighting?  Let’s say this sneaker-wearing employee is fabulous at her job, never late, and always has a great attitude.  Her footwear becomes even less important, although letting it go sets a precedent.    

The important thing to remember is that your appearance is a quick summary of how you want to be perceived, and in spite of the old cliché about books and covers, we absolutely judge people based on their exteriors.  What you wear to work is a reflection of how much respect you have for your job.  I want my appearance to say that I take my job, my co-workers, my customers, and my boss seriously. While you want your clothes to express your personality, there are parts of us that don’t belong in the workplace.  Like pajamas or workout gear. 

And with that said, let’s get one thing very clear:  leggings are not pants.  Don’t make me repeat myself.

Even in a role that’s customer-facing, while you want to dress to impress, you don’t want to make your customers uncomfortable by dramatically out-dressing them.  My own rule of thumb in such situations is to look professional but relatable.

Furthermore, suits are associated with The Bad Guys.  Think Star Wars – the rebellious heroes were a mismatched, ragtag bunch who saved their galaxy while dressed in comfy looking loungewear and orange jumpsuits.  Luke Skywalker basically wore a robe, leggings, and Ugg boots.  The evil storm troopers were strictly regimented and were outfitted in identical molded plastic with heavy, face-covering helmets.  Their uniforms erased their individuality, their creativity and their freedom.  Their leader wore a cape for goodness sake.  While both good guys and bad guys wear them (I mean, Superman, right?), there’s no such thing as a casual cape.

You know who else wears suits?  Lawyers and politicians, that’s who.  I don’t think I need to say anything more about that.

So relax, get comfortable, enjoy the freedom of a casual dress code, and get your work done.  And if you have any questions, let me know.