I always start by doing an op-shop / second-hand baby store shop. Last run for DS I got 4 t-shirts, 2long-sleeved tops, 3 pairs of pants/trakkies and a winter coat all in great condition and spent $35 total. I also buy a couple of really old things (50c each) so he's got something to crawl around in the dirt and wreck without me having to worry. Having done this, I feel I can justify a few 'nicer' things to complete his wardrobe.