I can totally relate to your post. Firstly I hate spending money more than you can imagine; I'm a real cheapskate. Secondly I'm setting up my own business at the minute so my monthly income is absolutely zero and will probably remain the same for many months to come. Having an empty bank account is one of the greatest thing for reassessing your priorities and making you question every cent that you spend.
It's difficult to give specific advice as you're in NZ and most on this forum are UK or at least EU based.
A few things I've learnt over years of being cheap and months of being skint:
- Branded isn't the be all and end all. In the UK we have Primark which is cheap and quite often nasty. If you hunt hard enough though you find gems. Particularly I'd recommend picking up accessories from places like this. It makes no difference whether your pocket square cost 99p or £20 (and I can say this owning squares which fall into both camps). Braces, ties, cufflinks, pocket squares, hats; having loads of these small items lying around to add something to an existing outfit is a really easy way of upping your game.
- Spend money on the things that matter to you. Ignore what other people think. For me personally I wouldn't buy cheap and nasty shoes as I feel they're a false economy. T-Shirts, jumpers, chinos, etc I feel are fairly similar so don't feel the need to spend crazy money on quality.
- Think tactically. I lived in a slightly rough area of Bristol until recently and always moaned the charity shops had nothing for me. Then I moved to London and started browsing the shops in very affluent areas. I've found Daks suits, Aquascutum raincoats and Tiger of Sweden three-pieces all well under $100 USD. Don't rely on hipster second hand shops for these; think of where they'll end up when their original owners ditch them and take advantage.
Good luck and let us know how you get on.