The Challenge of Dressing For Success

Photo Credit: Averain

In the "adult world"--you know, that place where real business is transacted, big decisions are made,
important meetings held--your attire is essential.  Blazers, ties, slacks, wingtips, pantsuits, heels: these are the not-so-secret handshakes to enter that banal society whose only mission is to allow you to be taken seriously.  And don't get me wrong: I want to be taken seriously. After all, I run a nonprofit whose mission is to tackle poverty.  The problem is that I also want to be comfortable, both physically and, more deeply, with who I am.

So what does that problem have to do with clothing? You see, many years ago I decided to eschew driving in favor of making the bicycle my primary means of transportation; and although in the intervening years I eventually succumbed to pragmatism and purchased a car, I do my best to avoid using it.  The challenge is that it's hard to square bicycling to the office and to meetings--in the rain, the snow, the cold, the wind, the searing heat--with the world's demand for sartorial splendor.  Nice clothes get sweaty, get wet, get wrinkled and generally don't stand up well to anything beyond the carefully climate-controlled environment of the cubicle.

I know, it's a silly thing: why not just put on a damn suit and tie, especially if it means I an more likely to raise funds?  One answer is that I've been stubborn about it.  Another is that a part of me wants to rebel (in an extaordinarily insignifcant way), to insist upon my ethos.

The Suit and Tie

I bring all this up because the other day I had to wear a suit and tie for a lunch meeting.  As expected, I was rather uncomfortable: it was extremely hot, the tie was strangling me and for whatever reason whenever I tuck in my shirt my back starts hurting (yea, yea, it sounds ridiculous...but it's true  I feel like I shouldn't move lest the damn thing come untucked).  But what I didn't expect was the sense of power that came over me, as though I were saying "Yes, now I am a serious man, a man about town, a man who gets shit done!"

My conclusion?  It's time to buy a nice suit, one that doesn't make me look, to quote Rachel Wall, our Head Financial Coach, "like a sailor."  Still, don't expect me to make friends with the local haberdasher. Whenever possible, I will choose to be pragmatic and will always ask, when shopping for clothes (on the rare ocassions that I do), "Do these pants have a gossetted crotch?  How will this shirt feel when cycling?"

Oh, and I couldn't resist mocking myself for wearing a tie (something I haven't done in years); in the photo above I am playing the role of the the jester whose buffonnery questions the world around him even as he acknowledges his own absurdity.