I actually looked around and couldn't find this thread anywhere else... so I thought I would start it since this is easily one of my vices.
Let's see... in college I started out with a hugo boss charcoal suit (actually exactly the one in this picture). I had it tailored at Richard Benett tailors in Chicago (great tailors and bespoke suit makers if you're ever in Chicago). It was my first interview suit and, being on a budget, I actually found it at Sak's off Fifth for a little under $300 which was a steal considering I had seen the same suit for $1100 at Nordstrom. Tailoring was $100. As I went in to different banks to interview on Wall Street, I received compliments on the suit from people in the bank that assumed I worked there. That's the ultimate test, since they probably paid 8 times as much for their own suits.
But as we suit connoisseurs know, off-the-rack suits can never really give you the nice fit you want. Heck, even an armani off the rack suit will have really nice fabric but the fit will never look as good as a bespoke or made-to-measure suit of inferior fabric.
My first foray into the high-end tailored suit world was with Ermenegildo Zegna. They offer made-to-measure suits with excellent cuts and top notch fabrics. I had one made in a very dark charcoal with squares. It's a 150's fabric so it has a VERY fine weave. Issue is that it tends to wrinkle very easily. In retrospect I would have gone with something a little more coarse for daily wear. Plus it would've been cheaper.
Overall the fit was excellent for a made-to-measure suit (essentially made-to-measure is the cheaper variant to bespoke in that they have pre-made templates for a huge variety of body types and they fit you to the closest one then tailor it). I was in very good shape then (body fat 15% with a slightly visible six-pack) so it looked REALLY sharp. I've got to dig up the pic and put it up and take pics with all my other suits. The suit came out to around $2000 (€1900) and then and only then I truly understood why suits can cost that much. When you put it on you really do feel... like the boss. Until your managing director tells you to finish some research that you know will leave you pulling back to back all-nighters sleeping and showering in the office.
I ended up purchasing another Zegna suit and a brioni sports jacket which I ended up selling.
My dream suit, however, will be made this fall (I need to get down to six-pack shape which means a lot of rock-climbing this summer). Norton & Sons in Savile Row, London used to make suits for Emperor William I of Germany. British suits also have that really nice hourglass cut in the waste that I think looks nice if you're in shape. Any recommendations on fabrics?
I think I will post comparisons next week. I hope other head-fiers are fond of classical clothing.