I have a confession to make, I am a bit obsessive compulsive when it comes to what I wear on a plane.  I make it my mission in life to make sure I am dressed comfortably before walking down the jet bridge.  I have changed in to “street” clothes in the restrooms of more airports this year than most people will visit in their lifetime and if being able to completely change outfits without any item of clothing or patch of skin hitting the bathroom floor were an Olympic sport, I would have a really good shot at medaling.

You see, I like to travel comfortably.  Really comfortably.

I would say that on 95% of the flights I take, I am in jeans, a t-shirt and flip-flops (assuming the weather permits).  It is what I am most comfortable in and actually what I feel most confident in.

Those who travel with me on a regular basis have gotten used to my obsession but this was not always the case.  When I first started making this a habit, I often felt judged by both my coworkers and fellow travelers.  When you are in sales or service, you are always on.  Just because you left the client’s office does not mean you are ‘off stage’.   One of the women I used to work for was a fabulous leader and was keenly aware of this fact.  She was always put together and on point.  I think my habit of being in t-shirt actually really bothered her for a while – until we unexpectedly sat together with a client on a flight back from a conference.

There I was with two of the most influential personas in my industry, having an in depth conversation about trends in the industry, future advancements and speculating on the next generations of tools to come forth……..

And I am wearing a Mickey Mouse T-Shirt!!

I literally wanted to crawl out of my skin (or at least that shirt).  Here I was, trying to make a name for myself and I am wearing a cartoon character across my chest.  I was left with a choice, cower and apologize for not being dressed ‘more appropriately’ or be confident in who I was rather than what I was wearing.

Of course the story has a happy ending and I managed to not make a fool of myself and in fact, that shirt spurred on conversations about our families, vacations and my obsession with the company that is Disney.  It also taught me a very important lesson, the clothes do not in fact make the man.  I firmly believe that the man makes the clothes. I was far more confident in jeans, flip-flops and a Mickey Mouse t-shirt on that plane than I had been just 4 hours early in a sports coat and tie.

The clothes do not make the man.  The man makes the clothes!!

Since then, I would like to think that not conforming to the khaki pants and blue blazer uniform of the typical business traveler has become somewhat of a trademark for me.  I even think that some of my clients/coworkers would be disappointed if showed up for a flight in anything but a t-shirt.  The message in all of this?

Confidence is more important than conformity.

I would rather lose a client/deal because I was transparent than win one because I put on a false front.  It really is that simple.

Life is too short to put perception ahead of transparency.  So travel in a t-shirt, or a bow tie, or yoga pants or a 3-piece suit.  Just make sure it reflects who you really are and the skin you are most comfortable in.

Can’t wait to see what you are wearing.