Ah you're the opposite body type to me! I carry all my weight on my boobs and stomach, very top heavy - I look like an egg on legs 
With the time of year, cold shoulder will probably be out soon, although I've seen lots of jumpers with them. Work out a new "uniform" for you that fits your lifestyle and then you can update it depending on fashion trends and if you like them. Velvet is supposed to be big this autumn but I hate it so won't go near it. However sportswear and animal print are also in, which I love so I'll probably pick up a couple of things.
I normally wear Nike trainers, Converse type pumps, brogues or flipflops with the skirt, but I live abroad. I have worn ankle boots which work well too. My skirt was from Glamorous not so long ago, but I've seen similar in ASOS.
Have you tried boyfriend/girlfriend jeans? They work well with the shoes above too. A A/W option could be an A Line skirt - in my head I've seen a corduroy type one that comes to the knee and with tights would look great.
Oversized check shirts over a vest are always popular in A/W, Topshop always have some great ones. Would you wear shirt dresses? I find them really versatile and easy to just throw on. With the jeans and tshirt, look for a trophy jacket or bomber jacket to go over the top, lots in the shops at the moment and just makes it look a bit different quite easily.