There is I think a common fallacy about clothing. Most men (and women for that matter) dress to please themselves or to please other people. This quote from Epictetus in Richard Torregrassa's new style book, Cary Grant: A Celebration of Style, illustrates a rather more compelling take on clothing:
Know first who you are, and then adorn yourself accordingly.
In other words, your character and identity should inform your external accoutrements. I think most men do exactly the opposite (e.g. feel better about themselves through fine clothing). Or, they dispense with the first part of Epictetus' advice entirely (e.g. dress without reference to character or dress principally to "impress" persons of interest).
Why is this point important? Because your character and identity are rooted in principles, concepts and ideas that are external to you. To put it simply, the question is whether you relate yourself to something greater than yourself or is everything just about yourself?
Cary Grant I think epitomizes what Epictetus admonishes us to do. CG displays an admirable consistency of the interior and exterior that I wrote in my very first blog entry. True style is a principle of consistency rather than the pursuit of fashionable conceit.