There is a little pocket of coolness just down the road from me in Darlinghurst. Walk down Riley street til you hit Oxford and cross over to Burton street.
In this pretty little corner of Sydney you can find Outre Gallery, an impossibly cool gallery that stocks amazingly weird and wonderful artworks that Id love to have in my home, things I didn't even know I wanted in the first place!
Dr Pong- so called because of the ping pong table in the middle of the room- is one of those casually trendy places that serves beer in red plastic cups, like those in American frat party movies, and hosts art shows. I had my birthday drinks here and it had such an easy, laidback atmosphere. Everyone took turns playing ping pong all night and while you inadvertantly smack the other patrons with ping pong balls, they're very understanding.
Across the street, in an old sandstone cottage is The Commons Local Eating House. I haven't tried it yet but I popped in there once when it was called Pond and the building has a cramped, homely feel. It serves French and Italian food and it sounds good.
Around the corner on Crown St is Pocket Bar which has a real Melbourne small bar vibe and they do really delicious savoury and sweet crepes but it gets really packed so you need to get there early to avoid the after work rush.