My most expensive shoes would be my RM Williams boots, which were $250 when I brought them 9yrs ago and now they are nearly $400 bucks a pair - so lucky for me they never wear out LOL. I usualy prefer to buy good quality stuff from myer etc on sale, but stuff that wont date either, like coats. I did buy a red wool pea coat from Ezibuy a few years back for $120 and that same year Myer had an identical coat for about $240 - so that was a bargain and it's still going strong. I don't go much for handbags but I did buy an oioi nappy bag this time round for $140 - I've never spent that much on a bag before.