You can dress well with quality if you comb the clearance racks and use coupons.
Not sure if you guys have Carson P. Scott out west but ours has 60% off racks with name brand quality clothes. They are a season or 2 old but I got some nice Nautica and Calvin Kline(sp?) summer kaki pants for $6 each after discounts, they started at $50 originally and they are great on cool days like today.
I can get nice shirts originally $50-60 bucks for $9-$15 bucks. The thing is you have to look around and wait for the stuff to turn over. If you go in needing something specific that is not on sale or clearance then you are screwed.
We have Lord and Taylor out here also. They are Higher end, not quite Neiman Marcus but very expensive. I was looking for a nice work shirt and found out they had a clearance rack also. I got some real nice Polo, Alex Canon, Abboud shirts that were $100-120 each for $15-$25 bucks.
It is all about knowing when the sales are (end of seasons) and checking in often enough to see what is new on clearance before it gets bought up.