0L Newbie (and anyone else), if you want to do this right as cheaply as possible:
1) Go to the nearest Brooks Brothers outlet near you. Buy two 346-stretch suits for $549, one navy, one charcoal. These suits are much better quality than Jos A Bank for the same price, and especially better than Mens Wearhouse-- they just aren't double canvassed, so they wont last 15 years. Get measured for a dress shirt, don't buy one there.
2) Take your Brooks Brothers suits to a normal BB store, they will have a tailor option that is high quality and inexpensive-- they wont overcharge like most places because they figured that you have purchased one of the more expensive suits and have rolled it into the price. My tailor was shocked that I paid "500 per suit," actually I paid 250 per suit (but didn't have the heart to tell him).
3) Find a Van Huesen outlet, or go online to a van heusen store (or amazon works too). Buy white or light blue dress shirts, no patterns or stripes, for around $21 each, using the measurements BB gave you. If you are really skinny or fat, buy the regular oxford shirts, they will make you look bigger, or conversely hide your curves. If you are in the middle (slightly overweight or buff), buy the fitted shirts because they will fit correctly. Either pointed or fashion spread collar should work, don't buy normal spread collars-- they are not conservative enough.
4) Go to the Nordstrom Rack and either buy Allen Edmonds Cap Toe Park Avenue or Fifth Avenue black shoes for around $205 on discount from $330, or if you want cheaper, buy Cole Haan cap toe, non square toe, black, lace ups for around $100. Also, while you are at the rack, buy cheap dress socks that match your suit pants or shoes, and buy a black belt.
5) Go to http://www.thetiebar.com
. Buy "traditional" (non-skinny) red or blue or mixture silk ties that are striped or dotted for $15 each.
Get a watch if you want.