When well-dressed men transgress, their clothing-related sins usually involve overt attention seeking with unusual styles and loud color combinations (often at the same time). That sort of attention clamoring never seems to apply to Luca Cordero di Montezemolo, without a doubt one of the very best dressed men in the public eye.
No, when Montezemolo errs, he is still wearing conservative clothing, well cut and discreetly colored. His penchant is instead to push the boundaries of sprezzatura, or studied carelessness. The idea is to show that one is not too careful with his clothes, which is of course more of an obsession than not.
For example, would anyone argue that the jacket in the center of the photo is unintentionally buttoned incorrectly? Caraceni never intended for that lower button to be closed, and Montezemolo knows it. But there are half a dozen or more photos online that show him wearing a coat cut to button to the center or top, buttoned instead all the way or to the bottom.