...and wet!
Hoping someone will suggest a style I already own and just haven't thought of trying 
I'm in Scotland - it is getting chilly and already raining fairly heavily more often than not. I commute to an office job (need to be fairly smart) by train, short walk at either end but need to do it quickly, but happy to change shoes in the office, so suppose the weather doesn't actually matter that much.
Not massively keen on heels and can't wear anything pointy (bunions). I'm a fast walker and apparently work in a very echoey office so don't want shoes that announce my impending arrival too much - I seem to STOMP LOUDLY in heels!
Trousers in question range from slightly cropped, narrow leg, to moderately cropped (I'm 5'3") and very wide leg. Fabrics vary from black stretchy suit material to terracotta cords to something green and floaty... I love them all in spring/summer with plimsolls or sandals, but at a bit of a loss for autumn/winter. I have no circulation and my office isn't the best insulated, so bare feet/ankles isn't an option very often.
My normal winter footwear is some kind of black or tan leather ankle boot, usually lace-up brogues, although I do own a pair of black Chelsea-style boots, somewhere. I wear these with lovely thick merino wool socks and feel amazingly comfortable and warm, can cheerfully face bad winter weather... but they don't go with cropped trousers (unless I'm doing it wrong).
Please give me some suggestions of what I could/should be wearing with cropped trousers this autumn!