Know thy rules
If you spend a lot of time reading blogs and forums on menswear and men’s style, you easily get the impression that there is a near-endless list of rules for dressing and that if you break but a single of them you are not considered well-dressed. While it is true that men’s style is confined by a relatively rigid set of “rules” that have developed over the last century, breaking one or a few of these rules is not a disaster. However, to successfully break rules you must understand why the rule is there in the first place.
A great case in point is the rule that you should always leave the last button of you waistcoat unbuttoned. Like many other things in menswear, the origin this rules is not entirely entirely obvious. The most commonly accepted explanation, however, starts with King Edward VII of England who happened to leave his last waistcoat button open for comfor. The aristocracy around the king quickly adopted it as a “fashion statement” and over the year it turned into a “rule” so that if you are not doing doing it today you can easily end up looking ignorant of dress codes. In fact, many tailor on Savile Row (and elsewhere) have taken on the tradition to cut waistcoats so that it is physically impossible to close the last button, thus ensuring that you follow this “rule”.
Despite knowing all these (rather trivial, you may say) things, I have nevertheless chosen to close the last waistcoat button in the photo above. The reason for this is simple - the waistcoat is just a tad bit too short and the trousers have just a tad bit too low rise. These two unfortunate circumstances has the effect that if I would leave the last button undone, there is a high likelihood that shirt and/or tie would peek through below the waistcoat, and that is in my mind a much more serious sartorial faux pas. So if you if you are breaking an established rule of dressing, it is good to both know why the rule was there in the first place and also exactly why you are breaking it.