I'm a "form follows function" guy. For that reason, I will always prefer an angled headstock to a straight one. Aesthetics do play a secondary role, however, which is why I much prefer the Tobias headstock over the Warwick.
Criteria for a good headstock:
- Angled design (none of that string tree nonsense)
- Straight (or nearly straight) string pull through the nut
- Symmetry near the nut (for aesthetics as well as hanging straight on the wall)
- Compact (saves weight)
- No obvious vulnerabilities (pointy bits)
- No all-inline tuners (purely an aesthetic choice)
- Compact and lightweight tuners
For this reason, the Tobias headstock is a thing of beauty.
The Warmoth house-style headstock is nice too, though the 4-string is not symmetrical near the nut.
The classic Gibson EB-0/Les Paul design, while pleasingly symmetrical, fails the "straight string pull" criterion in a big way, a shortcoming it shares with many high-end manufacturers.
The classic Fender designs, whether Jazz/Pre or Tele, fail on almost every count. The original Tele design is one of the ugliest things I've ever seen this side of a Wishbass.