NYC's Mayor Ed Koch?

I remember him as a good dresser.

Picking what you want for your own style involves being honest about your purpose. You cannot gloss it over and you cannot select style in a vacuum. It's probably not a great idea to copy someone else verbatim either.

Who do you want to be? Who do any of us want to be?  Brave assertions like "I know who I am" are clever but do not answer why you are interested in clothing. The assertion that someone does not want to impress anyone is likewise a lie to the self; similar to claims that one fears nothing. I do what I want regardless of those around me as much as anyone I've seen and yet, I dress to impress. Thus, who you want to Impress is important. To enjoy oneself is part of the equation but bear in mind that you can use clothing to change your environement's reaction to you. And the target audience can be the elderly ladies whom you want to invest in your limited partnership, or young, nubile things you want to think you're interesting to speak to. Are you trying to sneak up on people, deceive them, put them at ease, think you are cool, hip, beautiful?

Who impresses, you? And why do we wear tailored clothes? Do we admire the gentleman, the businessman, physician, intellectual, all of them? One has to admit to themselves that they dress for effect in order to grow and develop.

Are compliments more useful or criticisms?

Are the fits, cuts, colors flattering? Maybe you want to figure this out to purposefully "get it wrong", to elicit responses or wonder or further enhance the concept of studied nonchalance.

Time, place and manner. A legal standard but useful for choices in style. Where are you? Are you in the light of day, in fly over country, in front of the United Nations Assembly? What would you wear if you had to read a story to grade 5 children vs attending a piano recital with your significant other? What would you wear to not be noticed, to be considered prosperous or to disrupt the proceedings?

Does a great outfit matter if it can never be worn for your environments? I dress for my environment, my choices may be useless on a different personality or in a different location. I like to get people thinking about what gets them successful results for their purposes but not for my judgement. I am judgmental but I see different things than many on the forums do. What's more important, the smaller target audience or the larger number of unrelated people who may disapprove?

What are you comfortable in? Tight, loose, in between? Soft or hard fabrics, textured or smooth, old or new? Have I left some choices out?

What associations do you think of when you see an item of clothing or an ensemble? Is it universal or just the assignment you've given it. Knowing this is important. Denying it makes you the very thing you might deride. If you're judgmental, is it that all people are, or only you? Are you a control freak, do you not care about what others are doing? Do you think a tie is simply decoration or a mark of character? If you eventually saw a man in all plain solids had on a pair of multi colored socks would your opinion of him change to one of doubt or would you consider him a more normal, well adjusted person?

I am sure there is a lot more to add but I wanted to get the discussion started. Feel free to address what I've put or add other comments, questions or observations about clothes, why you put them on and what messages you think you are sending for your environment.