Jeans & A Tee

I have some friends that live by the jeans and a white tee rule. Personally I sometimes have issues with it. Its seems so safe and can be a bit dated - know what I mean? And I can't say that jeans are my first choice when I get dressed. Its hard to resort to jeans when you have racks of vintage to choose from - know what I mean?
I prefer to go by the
"OK, so I am overdressed - fuck you too"
rule (Rule #4 - The Shrimpton Couture Guide to Life)

But I have to say when I saw this outfit this morning on The Sartorialist the wheels immediately started to churn. I have those exact shoes and I have a vintage LV speedy - not the Sprouse print but same shape. I like the rolled cuff and the unexpected shortness of the leg paired with the more manly jacket and vest. I just bought an Etro vest edged with gold studs that would work this look even better that the picture, I think. Maybe I will do my own version of this one. One has to wear something grocery shopping after all right?

and yes that was tongue in cheek.....
or was it? ;-)