Many gents out there, and of course some ladies too, obsess on this dreaded subject: overdressing!!!

Let’s try to answer the question: is it possible to overdress? And possible way to deal with being overdressed or just simply feeling overdressed.

Anyway, this will surely make for a good discussion, so let’s get started.

Is It Possible To Overdress?

First let me try to answer the very common question: Is it possible to overdress?

This will probably come to a surprise to you, but in my humble opinion, it is indeed possible to overdress.

Now, let me try to explain my reasoning behind this: there are social occasions in which a suit and tie or any other type of formal wear can be considered overdressed and one can hardly come up with a good argument against it.

Would you wear your best 3 piece suit to a beach in the Caribbean? What about a double breasted suit with your most beloved silk tie with perfectly matching cufflinks (and let’s not forget a cool pocket square), to do manual labor outside? Would you wear a tux to a soccer match?

Aren’t these examples enough to confirm that yes, you can definitely be overdressed on some situations? I am sure you all will agree with me here.

But what about those situations in which it is actually expected and/or required to dress up? Can you still overdress?

Overdressing When Dressing Up Is Actually Required

Overdressed and Overeducated


You will find several occasions in which you will be expected to try to look your best: at work sometimes, a super important meeting with a potential client, that interview for the dream job, a fancy dinner, weddings, etc.

So is it OK to go all the way in these social situations and show how sharp of a dresser you are and try to impress yourself and everyone else with your style?

Well, it depends

In general, I am a firm believer that most of you are confident enough to be able to rock your ensembles, regardless of how bold they are, with the humble attitude that these ensembles call for.

You don’t want to be overdressed in your clothes and obnoxious in your attitude, that’ll come off as douchey!

The best advice I can give you for these situations is to make sure you look the best you can, even overdress to some extent, but try to tone it down a little bit. You can choose to wear a tie when everyone else is in a suit, but not wearing a tie.

Everyone is in full suit and tie? Well, you add the proper extra accessories: a great looking pocket square, a pair of classy cufflinks. Or why not go with a dressier type of suit? Instead of a simple 2 piece suit, you can rock a dapper 3 piece suit that will make you stand out from the crowd.

Wearing a full 3 piece suit, with a bold bow tie, all proper accessories and a fedora will probably be a bit too much for an outside reunion with your colleagues who are wearing a pair of chinos and the typical polo shirt.

Don’t get me wrong, it can be done, it might work, but you have to be careful when doing it – there is a chance your colleagues won’t appreciate it.

When Dressing Up Is A Matter Of Personal Style

For some of you dressing up has nothing to do with whether the social situation calls for it or not – it simply is your own personal style, the one you feel comfortable with and the only alternative would be a betrayal to your own self and your own personality.

If this is the type of person you are, then be yourself – just do it!

Overdress even if the event doesn’t really call for it, as long as you can look comfortable (and most importantly feel comfortable), you can definitely be true to your personal style.

The cool thing about this is that you don’t even have to *try* to overdress, you simply do and you don’t even pay much attention to it. Most likely people around you on a daily basis are already familiar with you are and your personal style.

As for the strangers who don’t know you, you bet they will judge you, but…

People will judge you anyway!

So learn to ignore the comments and wondering looks. No good can come of paying real attention to criticizing opinions, they will only lead you to self-doubt, which in turn will take away your confidence and then you’ve lost it all!

Master The Art Of Overdressing With These Few Tips…

Master the art

Ok so it’s clear now that you are dapper, you wear your best ensembles to any occasion and you don’t give a damn about the haters. Still, there are a few thing to take into consideration so your “overdressed” style will work:

  • Be consistent – if you claim that dressing up the best you can in every occasion is your personal style, then make it so. Don’t give contradicting ideas by overdressing today and wearing a t-shirt tomorrow.
  • Make your surroundings match your style – While you can feel this comes off as a bit shallow, it can be a bit weird to wear your power suit everyday while you drive an old, dirty car.
  • Be confident – Your personality makes more than half of your style. Always be confident when overdressing.
  • Be humble – I already mentioned this, but it needs to be echoed. Be humble and respectful in how you treat others.
  • Tone it down sometimes – Sure, it might feel great to be yourself and wear whatever you want as long as you feel comfortable, but it can be a wise choice to tone down a little bit.
  • Pay no attention to critics – Learn to ignore everyone else’s opinion on how you look. This happens to overdressed gents and underdressed guys.

Do you have any more tips to share? I’d like to know about what you think!

In Conclusion

Choosing to overdress can certainly be a tricky thing to do, but some common sense and being true to yourself is the best choice I can give. In the end, what you really want to do is express in the outside how you feel in the inside and that can never be a negative thing – maybe a controversial one – but never a negative one.

One last advice: overdress and don’t overthink it!

Leave your comments below!

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