My top list is as follows
1. Point Piper
Woolsley Road, all the way. The Elite.
2. Rose Bay
By far, one of the prettiest and nicest looking suburbs in Sydney. The tree lined streets, the beautiful turquousie colour of the bay, and the friendly atmosphere make it my personal favourite. It is upper class, however residents are usually much more polite and helpful than say, Vaucluse (whom I found to be rude and aloof)
3. Kirribilli
Has one of the best views of everything, and although while at first the whole idea of living "North of the bridge" might sound offputting, it really is an incredibly convenient place to live. It also has a great 'village community' feel, and the people in general are much less pretentious than their Eastern Suburbs counterparts. If it's good enough for the PM, it's good enough for anybody
4. Bellevue Hill
A bit too close to Bondi Junction for my liking, but still a beautiful area. Still close to the city, however you do feel like you are worlds away from all of the hustle and bustle. It's in it's own little world all together. It's probably our closest equivalent to Beverly Hills (USA)
5. Vaucluse
A great description that I have read would be 'the closest thing you will get to a gated community without actually living in one'. Very establishment, but it's way too 'flashy' for me. If it were a car, it would be a brand new, shiny bright red Ferrari. It's also a little bit impractical, just in regards to the inaccesibility with Public Transport.