(Great website and forums! For a couple of weeks now, I have enjoyed reading the thoughts of so many of my fellow gentlemen who are in open rebellion against the current tide of slobification! So, I decided to join and post a question of my own. [8)])
It is often said that part of being stylish and elegant consists in following certain rules. However, it is also often said that the most stylish individuals sometimes bend (or break) those rules. So, there presumably must be both a stylish and unstylish way to break the rules. What are
"the rules" for that? In other words,
how does one break the rules stylishly? (Use examples to support your suggestions, if possible...Gosh...sorry if that looks like an essay question from an examination. [}

] I am a philosophy professor, so it is hard for me to avoid phrasing things that way.

)
Two things that I have seen in various books and articles on style:
1. To break the rules stylishly, you must know that you are breaking the rules.
2. To break the rules stylishly, you must do so confidently.
To these I propose a third:
3. To break the rules stylishly, you must respect the more fundamental principle from which the rule emanates.
For example, two sartorial rules are that
'Double breasted suits should never be worn without a tie' and
'Cutaway collar shirts should never be worn without a tie'. Now, I break both of these rules almost every day. (My "standard outfit" for work is a DB, tapered waist, side vent, ticket pocket, suit with a cutaway collar shirt and no tie and top two buttons of the shirt undone.) But, I (perhaps falsely?) regard this to be ok because, in part I try to follow the more fundamental principles from which these rules come, namely:
'DB suits are more formal than single breasted suits' and
'Cutaway collared shirts are more formal than other collars (except wing, of course)'. It seems to me that the previous rules are simply applications of these two more fundamental principles. As a result, since it is less formal not to wear a tie, to stylishly wear a DB suit without a tie, I have to do something else to respect the formality of the DB suit. In the same way, to stylishly wear a cutaway collar shirt without a tie, I have to do something else to respect the formality of the cutaway collar. My solution is to wear them together. That is, to make the tieless DB outfit more formal, I wear a more formal shirt (and vice versa). In addition, I always wear a handkerchief in the more formal "4-points fold" also to increase the formality of the look. So, while I am violating the rules by wearing a DB suit and a cutaway collar shirt without a tie, I am still respecting the more fundamental principles that these are more formal items by wearing them together and with handkerchief in the more formal "4-points fold" . I think that a tieless DB suit outfit with a button-down collar shirt and no handkerchief would not work as well. That would be not to respect the more fundamental principle that DB suits are more formal. For it to work, there has to be some "sign" that one has recognized the more formal nature of the DB suit. Now, apart from the propriety of my example, what do you think of my rule 3?
Also, even if rule 3 works, there are presumably many
rules about "how to break the rules stylishly". Thoughts about the rest?[?]