So, to answer a few questions:
(talking workwear here)
I wear flat black loafers nearly every day, in winter flat black boots. I also have some flat white loafers that I like and wear those with some dresses.
I have a lot more problems with shoes for trousers, a LOT more.
Tights - yes, they are a pain, double knickers does help.
How to keep warm - if a cardigan, it must be a short fitted one, I don't do anything droopy. But generally, just wear one of those thin thermal tops from M&S underneath in winter.
Always have sleeves, I can't go bare armed in work - mid length sleeves are best, smart enough but not so long you always want to roll them up.
And types for apple shape:
I avoid anything flouncy. I can't do clingy. It has to have some sort of detail on the body (but not a peplum, too much material in the wrong place) OR a pattern.
Not too high necked, but not showing cleavage either.
I don't like anything much above the knee, nor maxi lower calf dresses (for work, fine on holiday).
I personally can't stand anything (top, skirt, dress) that is lower at the back than the front.
I'd wear this: www.debenhams.com/webapp/wcs/stores/servlet/prod_10701_10001_103030323673_-1
or this: www.debenhams.com/webapp/wcs/stores/servlet/prod_10701_10001_028030321233_-1
But not this: www.debenhams.com/webapp/wcs/stores/servlet/prod_10701_10001_33678+12671121_-1
Nor this horror: www.debenhams.com/webapp/wcs/stores/servlet/prod_10701_10001_103030332013_-1