The term “business casual” almost always sparks conversation leading up to whatever event has been labeled as such.  The scope of conversation ranges from friendly fashion talks debating the timeliness of the sweater vest to panic-stricken email chains to determine if it’s a suit and no tie or khaki’s and button down type of event.  I can only speak to the male perspective and I know that business fashion for women is much more complicated.  I mean I get stressed over my 4 choices of attire while women have a giant open area to work with as there doesn’t seem to be the defined scope that men enjoy.

Anyway, I always tried to keep my “business casual” conundrum limited by sticking to the rule that you can always dress down but can’t dress up on the fly.  Basically, if there is a question, I go up a level ready to lose the tie, hang up the jacket and/or roll the sleeves to match the room.  This general rule has served me very well and was easy until I tried the CarFreeBrad experiment.

As the weather changes here in Massachusetts, my attire choices will be less and less in my control but will need to be defined by mother nature.  I’m often torn between putting my suit on somewhere in the middle layers and risking a downpour/hot sweaty ride or packing it up as best I can and trying to carry it with me.  I don’t, as of yet, have a solid system for transporting a suit on my bike but continue to experiment.  But when my experiments go bad it usually ends with a crazy wrinkled and/or wet suit.  I’ve found it’s easier to transport a pair on khaki’s and a button down in a safe manner. But this defeats two tenets of CarFreeBrad.

First, my aforementioned rule to deal with “business casual”.  Second, my goal was to live my life CarFree not live CarFree as my life.

I’m at a unique crossroads in my life and understand/embrace the fact that I need to be ready to pounce on any and all opportunities that present themselves.  I’m not likely to close a million dollar investor or secure my dream job on the spot when one of these opportunities flashes in front of me.  But I’m acutely aware that the impression/personal feeling I leave behind will make or break that opportunity.  The harsh truth is that I can say all the right things, be funny, witty, likable, credible and super smart but if I look borderline homeless that opportunity will walk away with a dramatically different impression of our encounter.

I guess this problem will go on the list of unanswered questions for me to deal with! But I’m open to suggestions.