Say I had ~ $1000 to spend on a new bike, but I wanted it to be a "classic." My definition of classic contains the following:

Downtube or bar end shifters
all steel
relatively straight top tube
lugs preferred

Now, if it was to be a commuter, add these things:

2 water bottles (or at least one set of bosses and space for a clamp)
fenderable
relatively tall stem
wider tire capable.

That said, here would be my list:

Surly:
CrossCheck
Pacer

Fuji Connoisseur (although it would be out due to brifters)

Salsa Casseroll

Trek:
520
Portland

Raleigh:
Clubman
One Way


I could keep going, but long story short, if it looks like a classic, I'd consider buying it. I have absolutely no use for CF/Aluminum. IMO, they just look too chunky, most are hard to put fenders on, and CF isn't really up to the wet weather stuff like metal is.

ETA: As you didn't say what kind of bike you're looking for, I'd also throw in some city bikes, like the Pashley Soverign or Guv'nor, the Schwinn Willy or Coffee, Any kind of Dutch bike, the Flying Pigeon, or the Raleigh Superbe.

Although, if I was to go with a new bike, it'd probably be from the late '80's to early '90's. Then, you get aero brakes, indexing on the bar ends or down tubes (if that's your thing...it isn't mine, personally), and double or triple butted tubing, depending on your poison. IMO, a bike from that era is going to be more than modern enough to be comfortable, light and fast, but is already chipped in, if you catch my drift.