If you don't wear them, they're wasting space in your wardrobe!

Here's how I get rid of clothes like this (I used to be a shocking hoarder too!!):
Pull EVERYTHING out of your wardrobe. Then, only put the things back if you wear them. Not if you one day will wear them again (they'll be out of fashion by then). Have you worn them in the last year? 6 months? Put them straight in a cardboard box or opshop bag. No mercy! Same principle applies with shoes, socks, undies, accessories, make-up, toys....(well you wouldn't op-shop makeup I guess!)

The great thing about this method is that because it takes effort to put things back away in the wardrobe, it helps me to be more ruthless. I do this every 6 months (maybe more often) and find more things to give away I think it helps to do it regularly, because this last time I said 'well I said I'd wear this since the last cull, and I haven't, so obviously I don't like it, so I'd better get rid of it!'.

My trouble is also we don't have much money for clothes, but as DH points out, if I'm not wearing something (either because it doesn't fit or I don't like it), I'm not saving money by keeping the clothes anyway!

I think you'd be surprised at what you can survive on clothes-wise. Really, a few good pairs of versatile pants, maybe jeans and tailored pants or whatever your style is, a few plain tops and cardis and then cheaper accessories like necklaces, bangles, scarves, and a few pairs of cool and comfy shoes! When I think about it, I can spend a week in 2 pairs of pants, a different tshirt/top, 2 cardis, and the same pair of shoes!

A stylist sounds like a good idea too, I have a friend who's a stylist and says all her clients (and their partners) are always really happy at the end and at follow-up.