I have definitely spent more, but that was after 10 years of not really buying anything. I was never into clothes and, for example, was not given a clothing allowance in my teens for the simple reason that my mum knew I would never spend it! I also feel uncomfortable about throwing things out 'that still have wear in them' although I have done that more, recently.
I have never made really bad mistakes (because I have never bought on impulse) but of course never bought anything really stylish either. Since YLF I have allowed myself more leeway to try out new things and I have now bought a couple of things that are probably not great longterm purchases but are fun. I also upgraded from plain jersey tops to knits and am very disappointed by how badly they have worn. It was a useful stepping stone, though, towards woven tops, which I want more of.
Apart from that, the purchases I have made, especially ones recommended by Angie, have more than paid their way in my closet and look as if they will last, while alterations to some items in my closet have given them a new lease of life, which has not been expensive compared with buying new.
And of course I am dressed more stylishly and have lots of fun!