Clothing Dilemma (aka procrastination in poor disguise)

I have been lurking over at Pattern Review lately - it started out as innocent looking at the patterns, and getting ideas on things to sew for me. Then I stumbled upon the 2010 wardrobe contest, where participants are sewing a number of items, that can all go together. So all the tops go with all the bottoms etc. WOW! This is a little out of my comfort zone (ok....wayyyyyyyy out of it to be honest, 11/12 items that go together to be completed in just 3 months!), so lets just say I won't be joining in. But I am reading the thread and ogling all the story boards that members are posting - they all look fabulous.

I have also seen around the web, talk of SWAP sewing - (Sewing With A Plan). And that looks more my style - but, I don't know. Maybe I have sewing commitment phobia or it could just be procrastination :)
Looking through my clothes (most of which are RTW at this point in time), they are getting old, tired and just aren't my favourite any more. In fact most of them are from straight after I lost weight, and needed stuff that fitted. They are all pretty basic styles, jeans and knit tops mainly.

Sure I will continue to wear them, probably until they become no longer acceptable to go out in public, but aside from my favourite jeans, I don't really love them. I have never been one to care too much about what I was wearing - as long as it suited the situation/outing and were comfy, then I was happy.

But lately I have been feeling a wee bit too daggy, even for me. Mainly on the walk to school for some reason. It is rather cool in the mornings here, so I have been layering my tops, and the top layer is a particularly daggy brown knitted jumper. Oh it is warm, but man, paired with my mens, at least one size too big, cargos, and topped by a hat (yes, I wear a hat even when it isn't sunny - it keeps my head warm!), I am very glad I never stop long in front of a mirror - except to see if the collar of my t-shirt, under said jumper, is straight.

Maybe it is part of getting older, but I feel like I am missing something with the clothes I wear. I want to look and feel slightly better put together. I still want to be casually dressed, but a nice casual instead of a daggy casual. And even though I have never liked wearing skirts - I love the skirts with boots style I see. Any ideas on feeling comfortable wearing skirts? Not long ankle length ones though - they totally don't suit me - I need them to be about knee length.

I have a few ideas I am hoping to sew, but I tend to get overwhelmed just thinking about the whole prospect.
So far, I have patterns picked for my walk the kids to school wardrobe - a pair of cargo's from Burda magazine, and a Beala as replacement for my daggy brown jumper. I am also planning on making the 5 pocket jeans from Ottobre Woman - wish me luck - I have never sewn jeans before :)
Where to go from there though, I really have no idea! Anyone have any good book suggestions on dressing for your body type? Or site links? Or any helpful hints? I am going to have to do this again when summer rolls around, as that half of my wardrobe is possibly even more pitiful :(
Oh, and the kids won't stop growing, so they will need more clothes all the time.....

Cheers!