I’m sure many of you have read my recent blog post on how to deal with outdressing your boss. I have received lots of feedback and I know that it has helped at least some of you to come to a resolution on what to do about it.

Which makes me a very happy blogger.

But just as I clicked on “Publish”, I knew there were still questions left unanswered. Or maybe some other circumstances that the original blog post didn’t cover.

Well, I was right.  Last week I received a very interesting email from a friend from Germany. He uses the nickname StylishMenLostInOffice, so you can imagine what his question was about.

Yes, he has some troubles trying to match his job with his own personality and own sense of style.

The Question – Outdressing Everyone At Work!

Please take a couple minutes to read StylishMenLostInOffice’s question, I am sure many of us will feel related to his dilemma:

Click to read StylishMenLostInOffice's question

Hi there, I have read your two posts about issues on overdressing your boss. You have some solid points on that, the bottom line is 1 level over your boss and be confident about that. But what if your coworker is dressing in such a looooow standard?

Here is the situation. I work in the IT department of a Bank as a junior Project Manager. My team consists of mainly internal (hired by the bank) and IT consultants from 3rd party companies. Those IT internals are dressing quite casual, the best could be a button up dress shirt with jeans and leather shoes, but the majority are with Polo shirt / Pull over, jeans, with sneaker or sometimes Running shoes (what a match gosh!), The Worst? Unfitted T-Shirt with 70s buggy jeans with slippers!! Now what about my Boss? He is always wearing short sleeves button up shirt, formal pants (but not suit pans), and a jacket. Once in a month maybe he will wear Jeans too. I hate wearing Jeans at work, it’s so not formal!

I found that most of the people are in their 40 to 50+ years old, maybe that’s why they dress like that. I am a late 20 young men. I am new to the team and with a junior position. I have been trying to fit in by having button up dress shirt, suit pants, leather shoes. Sometimes if I have a suit jacket (no tie of course), they would ask why am I dressing good today. I always have to use the stupid excuse of I have a date. (They are all married so they don’t need to dress up or whatever).

Even if I am wearing a suit jacket, I still hate myself because it is actually not normal at all. The suit jacket and suit pants are not coherence, basically not a suit setup, just some business casual. While I was fine for several months, until recently….

I start to meet new friends, (since I was an investment banker before, my friends are still wearing in suit without tie), so when I meet with my friends, I feel so shit about myself. I know I work in an IT department, but still it’s still a BANK!

Last but not least, those external coworkers in my department, they were in suit, I told them about this dressing problem. They told me they don’t care, they like dressing in suit because they are young, and they feel more comfortable in their skin on this.

So Dear Ed, could you give me some advice? If Fitting in = sacrifice my personality, personal style, I think it’s not worthy. I don’t mean I want to wear a suit, but I do want to wear a suit without a tie, I will be fine with this, but based on my previous experience, whenever I have a suit jacket, they would asked… I wonder what else can I do?

Are there any style that is as formal as suit but will make it easier to blend in with the others? Yet showing I am as elegant as my friends (investment bankers?)

Eventually I still want to wear a suit (without tie) to work despite how my coworker wears. So my questions are..
1. What are some good ways to slowly blend in so it’s not like I have a sudden change of clothing?
2. I dont need to wear a full 100% formal suit, so do you have advice? maybe on some relatively casual suit, maybe with lighter colour so it doesn’t should like I “want to replace their job”, but I just want to “look fashionable as a young guy”

Thanks for your help!

Ed Answers!

casual office and coworker

casual coworkers are the worst!

First of all, thank you so much StylishMenLostInOffice for sending in this question. Believe me, I can imagine how challenging your circumstance must be.

Ugh, the dreaded IT department. Yeah, the place where no sharp dresser would ever feel comfortable in his own skin. And what’s worse, it’s not only IT departments that are shifting towards a more casual look – it’s happening almost everywhere now!

The good thing about your current situation is that your external team members are already wearing a suit and they couldn’t care less what anyone else thinks. That gives us a good precedent!

You can use this to your advantage. You can use your coworkers experience to gauge how dressing up yourself would be taken in the office.

Since you are already wearing button up dress shirts, suit pants and leather shoes, your goal of reaching a point in which you can wear a suit sans tie, is not one you are not that far from. It’s only the jacket you are missing.

This is good news, EXCEPT…

You mention previous experiences with wearing a matching suit jacket has resulted in coming up with the excuse that you have a date. WRONG! WRONG! WRONG!

Read this carefully, my friend: Do not ever come up with excuses to justify being yourself.

Go back and reread as many times as you need to.

Coming up with excuses is not only self-demeaning, but goes completely against your goal, so there is absolutely no need to do this.

Will you keep making up fake dates again and again? That’s not a very smart way to reach your goals!

No Legacy Is So Rich As Honesty

Here’s an idea: what if instead of the “I have a date” excuse, you just shrug off their questions and be honest about it: “I am dressing this way today because I feel great when I do so!

I know being honest can take a lot of guts, but being honest can make all the difference. It can magically open the doors for you to be completely open about who you really are and actually feel comfortable in your own skin.

Worst case scenario, you can expect lots of inquiries from your coworkers or boss.

What do you do in that case? You answer all questions with honesty. Don’t be afraid to add in some humor to your responses, this can make the situation feel more relaxed.

Once all questions have been asked and all answers have been given, the road ahead will clear up for you to dress however you want.

After this somewhat difficult period, you will be free to wear a suit and even have fun with it – go for brighter colors, add some cool accessories to your ensembles or even play with some dapper suspenders. (See inspiration to wear suspenders).

You might even start considering wearing a tie with that suit (I mean, really, if you are wearing a full suit you might as well just throw in the tie anyway!). But if you feel wearing a tie can be heavy-handed in your office, just skip it.

To Wrap It Up

Yes, you will probably be THAT guy, but THAT guy is who you are, so embrace it!

I hope this response gives you the courage to go ahead and try to be yourself – life is too short, enjoy it and have fun!

PS. Extra advice: never use phrases like “I hate myself for this or that”… Really, just don’t, ok? 🙂

Got questions? Ask me!

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