Before I even start this post, I have to let you guys know, this blog post is about a problem I struggle with constantly, so it’s probably not just you. My hope is that by creating this post and sharing it with you, I can also come to terms with what is the best approach to deal with the fact that outdressing my boss can potentially be a problem. So let’s take this opportunity to try to look at things from an impartial point of view, shall we?

This is one of those burning questions among many guys and if you follow this blog, this is most likely a question you have asked yourself.

Is It OK To Outdress My Boss (Or Any Other Authority Figure You Work For)?

Unless you are your own boss – lucky you – this question has probably crossed your mind more than once.

Now, most experts will recommend against outdressing your boss. And I have to be really honest with you, this is usually the best advice if nothing else is taken into consideration. But luckily for us, it’s not necessarily as black and white as it seems.

So I want to make this a fair game. I will give you a few reasons AGAINST outdressing your boss and then a few reasons FOR. That way you can be better prepared if it comes to a point where you need to defend your own style.

Reasons Against Outdressing Your Boss

Office suitYour boss might simply not appreciate it. Many bosses or people with a certain authority in an organization will consider an employee who constantly outdresses them as a sign of disrespect from the employee. For some, trying to dress better than your boss is another way of saying “I am better than you”.

Stupid and shortsighted? Absolutely!

But he is after all, the boss and sometimes that’s enough reason to think twice before outdressing him on a daily basis.

Take this as an implicit rule of the common work environment. And sadly, you will probably have to learn to deal with this and save your better looks for your free time.

Bitter coworkers. If you are dressing better than your boss, you are almost certainly also outdressing your coworkers. If your office staff includes only you and your boss this is probably not an issue for you, but most likely you also have coworkers, and I bet most of them won’t be thrilled to see how you always dress much better than they do.

“What should they care? Screw them!”

Well, not so fast! The fact is they probably will not like it. This type of coworkers will take your sharp dressing as a challenge to them too. They can go as far as trying to sabotage your excellent work (I am just assuming you match the quality of your work to your clothes here!). It sucks, definitely, but better be on the safe side with your coworkers too. Oh, if we could only change coworkers… sigh.

Has this been the case for you? How have you dealt with the comments or attitude from your coworkers?

Office environment. We just talked about dealing with individuals, but what about the overall office environment? The results are not too inspiring, I’m afraid. A few studies that have come to the conclusion that in office environments, it is always better to fit in with the group.

The same studies do show that it might actually be a good idea to try to emulate your boss’s style, so the conclusion is very simple: try to dress in a way that shows you are a part of your team, but don’t be afraid to go one step further to come closer to match your boss’s style of dressing.

Yeah, that’s pretty lame when you really want to stand out from the crowd. But not everything is lost. Keep reading…

You can potentially feel self-conscious. And it downright sucks to feel this way just because you feel or look different than those around you, even if you look better than they do, this can be a potential issue. If you feel uncomfortable, or self-conscious, you will definitely stand out but not for the right reasons. Trust me my friends, even if everyone else is OK with your outdressing them, if you lack the confidence, you will fail miserably.

Reasons For Outdressing Your Boss

Suit workYour boss might actually appreciate it. As long as you are not going overboard in your attempt to dress your best, your boss might actually appreciate this little quirk of yours. I guess a good rule of thumb would be to dress one level above your boss, but never more than that. Otherwise the situation can get a bit risky, even with a cool boss.

My best advice if you find yourself in this position is to dress just as well as your boss, but add a single extra detail to your ensembles that will make you stand out. Again, nothing too fancy.

Do you do face to face meetings with clients? Your boss will definitely be grateful you always try to look your best for the clients.

You can be yourself. I am sure some of you just don’t feel comfortable to have to dress down your very own style just to “fit in”. For some of you this might even go in detriment of the quality of your work, as we all know, great motivation at work can come from feeling comfortable in your own skin.

Be a trendsetter. I know, I know… this might sound a bit too wishful thinking, but who knows? You might actually be that person that takes your office’s lame and boring dress code to a new level of dapperness. Now, I am not necessarily saying all your coworkers will suddenly follow your lead and show up to work in 3 piece suits, hats and bold pockets squares every day. But I am sure you can inspire them to try to up their game in little steps.

The most important thing when dealing with your coworkers is to be really open about your love for nice clothes. Make it clear it is an important part of who you are, but doesn’t essentially influence your interpersonal relationships. They’ll most likely take it as a funny idiosyncrasy and really, we all have them. It just so happens that yours is nice clothes.

Increased confidence. Just the opposite of what I already talked about in the “against” section of this post. If you can wear your clothes with confidence and attitude, then by all means go ahead and dress as sharp as you want, as often as you want. With the correct confidence and attitude you can dress as a clown to the office and own it (nothing against clowns – except my clown phobia, but that’s another story!), so why would wearing a dapper suit and tie be a problem, then? (Read also: Mastering the art of overdressing).

Ultimately, It’s All In Your Attitude

Every work environment is different and every boss has a different personality, so unfortunately, I can’t quite give one-size-fits-all advice here.

One thing I am certain about, is that outdressing your boss doesn’t necessarily have to turn into a big issue at work, you just have to know how to handle the possible reactions from your boss and your coworkers. In the end, I am sure you and the rest of your office (including your boss) can learn to look past your “particular” sense of style.

So, to wrap it up, I guess the most important takeaway from this blog post is that no matter what you wear, your attitude must always match your clothes. Can it be risky to completely outdress your boss? Probably, but with the right attitude you can do it and save you all potential troubles that could arise. In fact, the right attitude can and will turn the whole experience into a positive one, of that I am absolutely convinced!

Over to you now! What is it you do for a living? Is it common for you to outdress your boss? If so, what has your experience been like? Please leave your comments. I am sure there are many, many interesting stories to be shared!

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