Well, I don't know as much about clothes as the rest of the crew, but I am an expert in having a tight budget
I would say that if you pay retail, Canali, Corneliani, and Zegna (not Zegna soft) are all very decent suits-- much better than Hugo Boss or Armani le collezione. Canali and Cornelani should cost about $500 to $600 on sale or at Bluefly, and Zegna might run about $900 on sale at a department store. I'm sure you can get much better brands on ebay, though for under $1,000. Others on here have better experiencethere than I do, but I would look on Ebay for Brioni, Oxxford and some of the other higher ends to see of you could get them for $1k or under. I think I saw a Zegna Napoli Couture suit for under $1k the other day, and as I understand it, that is a very fine suit indeed.