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A couple of things:
It is ALL about the fit. If it doesnt fit, its worthless. Coats can be taken in a little bit, but it should be damn near perfect when you try it on. Like others have said, go to a mens clothing store (I personally prefer Jos. Banks, but thats because most of the clerks there know me and my family by name and how we dress... Go wherever you want). The difference between a well dressed man and a man in dressy clothes is the FIT. I cant emphasize this enough. Once you find the basic coat size that fits you, memorize that number. For me it as 40 Regular, but you are quite a bit larger than me, so it will be different.
Its also about the small things. Find shirts you like, and then--and here is the hard part--pick the types you like. There are many different collar/cuff combinations. No buttons on the collar of a shirt that will be worn with a tie. I also like French cuffs (no buttons on the cuffs, they are folded over and use cufflinks to fasten them). French cuffs, however, should not be worn without a coat, it looks too gaudy.
As for suits, start with a dark grey/black or blue (or both). Again, make damn sure it fits you. It is no good if it doesnt. And be prepared to spend some money. You shouldnt have to spend more than $500 for a good suit (unless you are some really uncommon size), but a cheap suit looks like a cheap suit. Dont be that man. Also, you will need a good navy blue blazer (and no, dont wear the blue coat from your suit, they arent the same thing). And slacks. Look for some nicer pants to go with them, your standard Dockers dont look all that good. As for shoes, brown and black should start you off fine. Dont wear shoes that are of a lighter color than your pants (generally). This means dont wear brown shoes with a black/grey suit.
Its all about the small things (and fit, like I have said). Anyone can wear a suit, but the person who is well dressed is the one who gets it all down.
A lot of looking well dressed also comes from knowing how to wear your clothes. This sounds odd, but a lot of people just dont know how to wear their nice clothes. Stand up straight, dont hunch your shoulders, be confident.
Oh, and regardless of the number of buttons on a coat, you never button the bottom button. Thus, if the coat has 2 buttons, only button the top one. Three, button the top two.
Im sure Ill think of some more later.
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"Good people do not need laws to tell them to act responsibly, while bad people will find a way around the laws."
--Plato
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