what footwear/legwear to put with winter skirts & dresses?

[EsmeCordelia]

I've had a pair of DM knee high boots for 14 years they've probably worked out at about 1p per wear at this stage. However, I am now in my mid 40's and need guidance as to what on earth I cover my legs and feet with when I wear skirts and dresses in winter. I live in a country village so walk to and from work/school/shops so need footwear to be comfortable but not too hideous. I love Fly London boots but their knee high boots look like wellies! Are knee-highs even still in fashion? I do sometimes wear ankle boots and tights and skirts but am not sure I don't look embarrassingly awful. I really am clueless so any pointers at all are welcome.

I had the same dilemma last year, when I decided to stop wearing trousers all the time and get a couple of skirts. After advice on here, I bought a pair of knee length suede flat boots and a pair of brogues, both to be worn with opaques, or woolly tights when it was really cold. I like ankle boots, but my 20something DD told me they were OK with skirts on YOUNG people !! (I'm early 60s).

This year I am considering defying her. It does depend on the length and style of skirt though - I'll wait for more knowledgeable people to tell you what goes with what, as I don't have much clue.

I bought some Fly bought last year, they are not knee high and they do look nice with dresses They are lovely and comfortable but dont like even a hint of wet on them

London Fly

I do not proclaim to be a fashionista but I love my slouchy 80's boots with dresses and skirts in Autumn

I live in town and need something that can cope with me carrying groceries over slippery, wet cobbles without looking like I've walked in through a field. Last year I lived in a pair of black ankle boots and a couple of pairs of brown high calf/knee boots, none of which I'm entirely happy with! I've got over the knee boots but I don't feel comfortable trotting around on my own in them, I fear they draw the eye!

I'm hoping to find some black, leather boots with a chunky, block heel and a good grip. I will not go near a Clarkes-style mum boot with a wedgy, wobbly slight heel. I think the heel needs to be a couple of inches and definitely separate from the sole, iykwim. I also think I want a couple of inches clear between the top of the boot and the knee. Definitely leather so you can scotch guard them every few weeks. Does that sound reasonable, do you think?

Double I think that the ultimate we're all looking for...

OP, I have a pair of DM knee high boots, I love them and will still be wearing them
I also have ankle boots, and in 40's, still wearing them, just bought a suede pair with a flared heel from Topshop.

I've noticed a lot of biker style boots on-line.

These could be good? I'm not 100% sure about the laces though. They'd help with the adjustability but are they the only fastening? Is there a zip on the side? Would they be a total PITA to fasten every time and do they give it a bit of a Victorian maid vibe?