Can't help as I am as lost as you are. I have ideas on what I think would look nice but they never seem to. I am stuck in a dreadful rut of jeans and t-shirts as I can't really afford anything new and different and due to fluctuating weight I have a hangup about fitted clothes. I know they are meant to accentuate your curves and make you look slimmer but I feel they will make me look like a sack of spuds with string around the middle
Is there anyone (celebrity/actress etc) who's look you like. They pay thousands to stylists, so don't feel ashamed to use their look as something to base your makeover on. I have about 10 women in the public eye that I follow, as in style gurus. Buy some mags - Look is a good one, Grazia okay. Book yourself in for a makeover at Bobbi Brown or Benefit, BB charge if you don't buy a product, so even if you buy a mascara you've got your money's worth. Benefit do freebies I think. Then visit a hairdresser with some ideas, or even have a look at the B&S board. Clothes wise, go on a fantasy shop visit, a lot of department stores (even Top Shop) have style advisers who can help you choose - or experiment. You don't have to buy. Have fun! Enjoy!
It's really hard to say without actually looking at you and what sort of thing you wear now iyswim, but careergirl has some good pointers, take a look at some celebrities you like the look of, and if you're not confident, just add an element of what they usually do, so for example, if you like Nicole Richie and her more relaxed look she does: skinny jeans, ballet shoes, t-shirt, floaty scarf and sunnies . If you like the idea of a more classic look, think Emma Watson: cigarette trousers, fitted shirts, nice bag, mac that sort of thing ... HTH in some way !