Random Rant from earlier, thought it might help.
Easiest way to get a very diverse wardrobe is to go to Brooks Brothers and get sized and talk fashion. Then buy a few dress shirts/ties since that are almost universally appreciated, not a bad price, and you wasted the salesmen time (I assume they are on commission, if it is like where I did retail, small items like ties and shirts have a higher %, so it compensates for you not being economically or self-aware enough for a BB suit, yet).
Use your new knowledge (and, if possible, a fashion-conscious friend, hopefully of the bangable variety) to go to a lower-cost clothier (JAB, MW, Haggars) and be selective, but bold. Every large suit store and company has some good finds. Keep in mind that worst case, you are out a hundred dollars, but can normally at least salvage some decent slacks.
Then take aforementioned shirts and new suits to a tailor. Buy some collar stays and an iron.
Try to wear the suits when they are not needed, just to see if you like how they look throughout the day, as well as to see if you get any comments or stares (No matter how attractive you are, stares are always bad, though second glances are good). Get comfortable wearing suits.
Some suits won't pan out, save it for weddings of family members you don't care about.
You will also find that your collection is lacking in a few key components (e.g. you only really have one tie that goes with the shirt you really like, or that you need a brown belt) Use the internet, outlets, or sales to fill those gaps. You can get away with a Sears tie, or a Walmart belt if its an deliberate part of an otherwise better-designed outlet.
Then as you get a better idea of what you like, what fashion terms mean, sizes, and a good tailor you can pursue two tracks:
1. Buy last year's suits at a startling low price from an online dealer with a good return policy (e.g. Overstock.com). Male fashion doesn't change fast enough to be worried with looking out of date (and I suspect, even if it did, lawyers wouldn't now the difference). Some people do this with shirts as well.
2. Invest in a few well-planned and expensive items, such as a BB suit/blazer, nicer shoes, or a classy tie clip/watch.