Sartorialists have it hard. How far should one push self over tradition, style over tradition, and whimsy over tradition? Many say what looks good or what you can get away with. Truly no one knows for sure. After all, Mr. Brummells and the Dukes of Windsor are only born once every so often. I advocate the Golden Mean; find the extremes and try to hit the middle. That is where your aim should be. Sometimes more dandy than tradition other times not. To paraphrase Antongiovanni in his book, "The Suit," sometimes age and position in life make it prudent to avoid dandyism. His example is of a young professional out dressing his superiors; he only does so at his detriment.
So, take caution and know your place in life. Exploit your gifts and use restrain when needed.
For more on this topic pick up, "The Suit," by Nicholas Antongiovanni and visit LeDandy's blog. He discusses the topic here.