Welcome to the bastard world of online ordering.
Essentially you want
- a black cap toed oxford
- a dark brown brogue
The black oxford will get you through your most formal occasions (church, weddings, funerals, job interviews etc) whilst the brown brogue is still formal enough for work but can be worn on dates or to weekend lunches.
In terms of work, ideally you'll be rotating them daily so that the leather has an opportunity to dry out.
Loakes 1880s are a fantastic place to start, there are a handful of places in the city you can try them on but you'll end up ordering them online due to the Australia tax. C&Js are a nicer shoe and more expensive, but have the advantage of a few bricks and mortar stores in sydney and Melbourne. Anything beyond these and you're playing a game of diminishing returns.
In terms of looking after them, you want:
- a leather conditioner - saphir renovateur
- a shoe cream the same colour as the shoe - saphir creme
- a pair of shoe trees
For all of these I'd recommend ordering from double monk in Melbourne who have fantastic prices.
Once you have these, I'd recommend looking at a boot - either an chelsea from RMWs or a pair of chukkas, which can take you from the pub to any formal occasion.
At this point I'd warn you to stop. Anything beyond this and you've well and truly gone beyond the point of diminishing returns and into the world of the SFer which involves long hours of depression flicking through eBay, buying shoes online and bitching about lasts and 'shoe hierarchy'.