From a fashion perspective, the traditional rules don’t apply in fashion anymore. The rules of no white after labor day; match belts, bags and shoes; women over ___ shouldn’t wear ___ etc., were created decades ago. The world has changed since then, and so have fashion rules. Now, there’s much more opportunity to wear what you like, express yourself, and only wear what’s flattering, regardless of the current trends and rules of years gone by.
From an image perspective, it’s useful to look at the effect of breaking with tradition. What does that say about you and what is the impact on other people?
If you are an innovator or creative in the way you work or live, then breaking the old rules is consistent with who you are, what you do and makes sense for your image. If you are in a traditional industry or social setting where stability, predictability, and safety are important, then breaking the fashion rules would create an inconsistent message in your image.
Following or breaking the rules can help you connect with others more deeply or create disconnection. If the people you are working/meeting with are rule-breakers, breaking fashion rules will help you connect with them. They will appreciate your cutting edge approach and have a tendency to trust you more. If you follow the traditional fashion rules, you risk undermining that connection.
If they are more traditional, then breaking past fashion rules will create disconnection. They may make you wrong for breaking the rules and be distracted or put off by your disregard for tradition, and you risk loosing their respect or attention.
As always, the “right” answer depends on who you are, what you do, and who you are with.