Today, in the effort to bring you a more well-rounded blog, the first in a series: as a man-about-town, our resident etiquette expert will answer reader questions on various DC-related topics of doubt, areas of concern, and romantic quandries.  To ask a question, please post in the comments section.

I’m the guy everyone comes to vent to and get answers on their problems.  I have been in relationships with an array of women that, if made into a Superbowl appetizer tray, would be significantly impressive.  I am a hardcore ENTJ and do not let emotions get in the way of my decision making.  At the same time, I am a positive driving force that inspires those around me to be happier and make good decisions.  I joked with Miss DC Style that I should write a relationship advice… screw it, any advice column.  Ready?  Here it is.

Dear Rob,

Is it alright to wear tennis shoes on the Metro on my way to work?  I know they don’t match my suit and look kind of weird, but they’re so comfortable!

Since you are even writing to this column, and you are focusing on a comfort-versus-fashion question, I have a pretty good sense for who you are.  I am going to say go ahead and wear those shoes.

Why? Because no one is meeting you based on your looks alone.  The people who do want to meet you will most likely appreciate the practicality of your tennis shoes.  If you are one of those well dressed ladies who uses her brain as well as the rest of her assets to push her career forward (and I say this only because it is a fact that attractive and well dressed people get further than those who do not take care with their style) you would never be asking this question in the first place.

But wait, what about the anomalies?  Not the awkward nerd who should always go practical and not the hot bombshell who would never be caught dead in tennis shoes because she knows that fashion and pain go hand in hand, but the alternative girl who gets a wild pair of comfortable tennis shoes that go with her super hip, large rim plastic glasses and her homemade wool hats and such.  How does she look cool AND wear tennis shoes AND be comfortable?

Because she doesn’t care what you think and belongs to that club… however secretly, she may very well care what her other alternative friends think.  So at the end of the day the reality is that it’s all about who you are and what you are trying to say with your choice.  Are you trying to scream practicality, do you get hip tennis shoes to straddle the line, are you the type who doesn’t mind suffering for fashion’s sake?  Or do you just not care and you can’t believe that we are discusssing this topic?  Figure that out and make a choice.

It’s simple.  Shoes or not shoes.