When Work Attire Doesn’t Work

It’s 7:45am and you are settling in to your cube getting organized for a full day. You hear rustling over in Morgan’s cube, grateful that he’s a bit early too. You need clarity on the July forecast prior to the 10am Ops review. You enter Morgan’s work space to find him looking less than office-ready. Your facial expression (akin to horror) must be leading because you’re greeted with, “Hey boss. Hope it’s okay I’m lookin’ a little casual today. I don’t have any meetings so I thought I’d hunker down at my desk, and no one would notice.” Your face is a study in confusion and disapproval. Morgan’s ensemble (to call it an outfit seems too generous) is a tossed salad of baggy joggers, a hoodie with paint stains, finished off with sneakers that would be condemned if they were a building. You wouldn’t wear this clothing combination to walk Rover, and yet Morgan walked the public hallways to get to his desk [cringe]. You quickly relocate him to the nearest conference room before any VIPs get a glimpse. Now you need to find the right words to respond to his “Hope it’s okay” greeting when this outfit is anything but okay.

Would it be a disaster to let Morgan sequester himself today given his meeting-less schedule? Probably not….until an emergency drags him (and his junky joggers) into a discussion with a senior leader or worse …a customer. The fact that Morgan thought it was okay to come to work dressed like he’s ready to clean out his car is on him …and on you. It’s as sloppy as Morgan’s apparel to ignore Morgan’s lack of judgement. Just as you provide clear directives for targets and tardiness, it’s also your responsibility to establish what can and cannot pass as workplace-appropriate dress.

Whether your team member’s ensemble is too casual or too flirty or too odd (think Halloween costume or ballgown at a budget meeting), you will need to manage your emotions while you manage this situation. No cheap shots and no digs masquerading as jokes. Starting with “Morgan, I confused you with the Grubhub driver” might be too bold. Anything that sounds like, “I can’t believe you thought this outfit was acceptable. You should be embarrassed. It’s making me question whether you’re a good fit for our organization,” is an overreaction and not helpful. Your colleague made a fashion faux pas, but you’ve made a managerial mistake by leading with shame instead of guidance.

Let’s circle back to the moment when you realize Morgan is not your caffeine courier. Instead of letting him justify those joggers, take the lead with,

“I certainly understand why you thought that today felt right for a relaxed look, but let’s think more broadly about why we care about dress in the first place. This is about how you represent yourself and this company. Your brand. Even on quiet days, your brand is on display. I know you have aspirations to move into a role of greater influence someday and consistently demonstrating that you are ready for that responsibility is important. How you choose to dress for the office is about taking care, looking prepared, demonstrating good judgment…and, today, you missed on judgement." 

If Morgan resists or reacts defensively with “I’m no less of a professional because of how I’m dressed,” offer empathy (he’s not wrong…hoodies are really comfortable) but not approval.

“I understand, but when it comes to workplace attire, appropriateness matters. Take the next hour to go home and change.”

If Morgan’s meeting-less Monday gives him an opportunity to work at home that day, consider that option too.

Let me be clear, this is not about a policy violation (see page 93, paragraph 3, line 2). Poorly skilled managers default to employee handbook text because they don’t have the words to explain the policy’s rationale. That policy was put in place because someone, at some time, used poor judgement that impacted their brand and possibly the brand of the company. They were (or made others) less productive than desired. Whether we like it or not, appropriate dress for your workplace promotes productivity, reduces distractions (my-plaid-skirt-uniform-be-damned), fosters equality, and might even enhance safety in some environments. It establishes professionalism, sets a standard, and encourages employees to present themselves in a way that reflects the values and image of the organization.

Of course, appropriate dress should be addressed during an employee’s onboarding. A simple yet specific set of guidelines can clarify what types of clothing solidly represent your organization. If your company rejects jeans and joggers and embraces ties and structured blazers, make it explicit. If casual Fridays are allowed, be clear about what ‘casual’ means. The better thing is helping Morgan distinguish between clothing for the weekday and the weekend. Guidelines guarantee that Morgan will get to keep his joggers, and you get to keep Morgan. A comfortable win for the entire team.

“If you’re close with someone younger than you who you believe is pushing workwear boundaries, you can start by simply engaging in a judgment-free conversation with them about their fashion choices. It’s OK to be curious and ask questions — you might learn something about them and style! And if you’re not satisfied with the response and feel close enough to the person to go further, you can always ask them, ‘How do you want to be perceived?’ and see if that opens up a conversation about how they present themselves.”

Kirstie Mitchell, career advice expert, Careers by Kirstie

“If you’re worried that doing away with dress codes will cause employees to take it too far (they’ll show up in pajamas), know this: the slippery slope argument strikes at inclusion. You need to trust that your employees will exercise good judgment and, if and when a few don’t, have one-on-one conversations with them instead of closing the door to belonging for everyone.”

Ritu Bhasin, author, The Authenticity Principle

“Whatever your dress code is, you need to communicate it in a simple and effective manner. I live by the rule that simple is always better. Simple will create simplicity, while complicated promotes complicated. Every company and industry is different. When creating your standards, keep simplicity in mind, what is important to the company, and what is important to the employee.”

Adam Mellor, human resources council, Forbes

Don’t stop now! Learn more from a few of our personal fav resources below:

Disclosure: The resources shared and listed by KKL & Co. are those that have been evaluated to be of high value to our leaders. We are proud affiliates for some of these resources, meaning if you click a link and make a purchase, we earn a nominal commission at no extra cost to you. Please don’t spend any money on these resources unless you believe they will help you become a better human.