I have a few pairs of certain styled shoes that i like to wear in the autumn. Heeled boots, loafers and flat boots. I like to pair these shoes with all sorts of different outfits, i think they especially work well with skirts, shorts and blouses, but the loafers work well with pretty much any look or outfit.
I purchased these boots earlier this year in a charity shop, and i wore them a lot in the january time of winter. They give me a lot of height with the heel and add a bit of edge to any outfit.
I purchased these boots about 3-4 years ago on ebay, they're the comfiest boots i've ever owned and they go perfectly with dresses. I don't think i'd pair these with jeans and casual outfits as these boots are a bit TOO casual to wear with jeans and a t-shirt, but if you pair it with a dress etc. the boots will harmonize with the outfit a lot more.
These Russell & Bromley loafers that i bought from a charity shop (for £5 what a deal) about a year or so ago were a the shoes i wore the most last autumn and winter. I wore them with everything as they're just so versatile, i think they dress up any casual outfit as well, and these would be the perfect shoes to pair with jeans and a cardigan.