I agree with nordstroms, but you're right, there is definately a fine line between expensive looking and high maintenance. I personally like to do what orangeeyecrayon does - buy from many different stores but with a particular 'look' in mind.
i can think of the stores i would try in australia, but I don't know any american stores. It's so tough though, many australian stores are extremely expensive designer boutiques, with really 'out there' one of a kind, overly 'runway' type pieces - that aren't even neccessarily attractive. It's like there is a tendency for people who really ARE rich to go for the 'I'm so rich I look like a hobo, but these jeans cost more than your monthly salary' look.
So, i guess more than the 'you cant afford me' look, I prefer 'i'm sleek and professional and well dressed' - mainly because I KNOW that i'm not rich, and there's nothing as sad as a try hard, which is what can end up happening (especially in my case, LOL)