Knee High Boots
Not the nasty stripper kind but the ones that are going to keep you feet warm and dry. A low to no heel is good for hard core walking (and shopping) without you feet giving out after an hour. Make shore that they are not too tight on your calfs so that you can wear extra socks in the cold.
A coat that is mid calf gives better protection from rain and cold wind than a jacket at waist or hip height, no one wants to have wet pants all day or sit straight into a puddle of water at the bus stop. A good looking coat can take a winter outfit from good to wow.
I have only recently become a convert to leggings, I am a firm believer that you shouldn't wear anything that you wore as a child, but after using them to wear for bed or to exercise in I found a grate trick. Not only can you wear them under a skirt on there own or layer them over a pair of tights to keep extra warm. If you get the leggings with a skirt band you can flick it up and keep your back and tummy warm if it is an area that gets cold.
Wool and Tweed
Everyone knows that wool is one of the warmest fabrics and worth paying the extra for warmth than buying something that looks warm instead of something that is warm. Tweed is a very versatile fabric with many different colours and textures. I like to wear grey or brown tweed and keep colours for my plad/tartan wool skirts.
All Images from etsy