I always end up in jeans. I crave comfortable clothes, but feel I might be prepared to stretch to leggings. I'm a size 8-10ish, pretty much straight up and down. Please show me how to wear the look (and suggest where I can buy some leggings). Feel so unimaginative, so please help me out.
Don't buy leggings....bit dated now and only Kate Moss could ever really carry them off without a dress over the top. Besides which, your ankles will get cold now!
Invest in a pair of great boots and go mad with coloured/patterned or simply black opaque tights and great dresses, there are loads of nice, comfy ones around, especially knitted ones at the moment. You can still be comfy and casual but will feel and look so much better. Look at Zara, H&M, French Connection for inspiration.
If you are dead set on trousers then leather or skin tight rubber-like ones are in this season, with big chunky knits on top - maybe not too practical for the daily park/school run tho .