Seems to me you're exactly the target demographic for Suit Supply. I've been in there and was fairly impressed with what I saw for the price. I'm in DC too, and there isn't much here in the lower priced end unless you go with a Macy's...
the t shirt should be white or light grey, and should have a v neck cut low enough that it can't be seen under the ocbd that you're wearing on top of it
http://us.suitsupply.com/on/demandware.store/Sites-US-Site/en_US/Home-Show
They're mostly $469. If you're in a city where they have a store, it's definitely worth stopping in to try on. If you're not, it still might be worth buying...
I forgot to post a thank you and picture of the tie Hendrick sent me in the free tie giveaway...sorry about that!
The tie is definitely nicer than I expected and easily worth what he charges for it. The silk is a little thinner than my...
Propersuit.com
They have the same fabrics as KW, but you get measured in person. I have two suits from them. The first fit well, the second is perfect.
full canvas, and they start at (I believe) $750.