I am a nightmare as I always struggle to find what I like and rely on one pair which I wear to death so happy to spend on them if they are "right".
I don't do pointy toes, I can't wear heels, don't want "dress" boots, something practical and preferably waterproof and warm. I had a pair of north face "trainer boots" for five years and loved them.
I am probably going to buy these if I don't see anything better.
I have a pair of ugg biker boots that I got last year still going strong but they are a bit clumpy and not waterproof. I have huge calfs so can't wear long boots.