A denim or cord skirt (just-above-the-knee length, or mini if you're brave), and some flat boots (worn with tights or leggings) would break the jeans rut without it being too much of a shock to your system. Alternatively, different trouser styles. I don't wear trousers much, but love my wide legged pair which I wear with a vest top and little cardi.
I like denim skirts in winter with thick tights and boots - practical, warm but a bit more dressy than my usual jeans and t-shirts. I've also finally got round to returning to leggings (I have a problem with going back to things that I last wore when I was about 15!) but have just got some nice ones and some long jumpers in a range of autumnal and winter colours which again are practical and very cosy (there's a theme emerging here isn't there lol!). I'm still trying to work out my footwear requirements although I'm sure the Merrell boots I just bought on the recommendation of any earlier posting will fit in well with this look. Have to say, I'm not really that good at embracing new looks either, so I'll be watching this post with interest incase someone comes along with some good ideas! Good luck
3rd vote for knee length denim skirt and boots, also lots of skinny/slim leg cords around which look great as an alternative to jeans. Also ditch the t shirts and go for slightly smarter "tops" that have a bit of shape/drape. I team them with little cardis for warmth (or even layer a long sleeve t shirt under them). Just looks so much smarter than a t shirt.
Dont underestimate the power of accessories, a nice scarf and a few bangles really make all the difference too. Dorothy perkins have loads of nice cheap bits and bobs (also good for tops at the moment)
I was thinking maybe casual dresses/tunics that I could maybe wear with leggings as they're a bit more toddler friendly than a skirt as I seem to spend my day diving to catch one of the DCs before they plummet off something they shouldn't have been climbing on