Ankle boots?

I no longer own any casual shoes apart from two pairs I bought for weddings which are not actually very comfortable. I also go from sandals to boots and jeggings for the colder seasons. However, I have just bought some black suede ankle boots from Clark’s which I intend to wear with dresses and tunics with coloured thicker tights when the weather gets cooler. Relatively flat and very comfortable. I cannot cope with heels these days.

I always wear ankle boots nowadays. I go from sandals to ankle boots. I like Reiker they are so comfy, I've got them in various colours. Autumn/winter I don't wear anything else, they also stopped me 'tripping'.

Have you tried Lisa Tucci shoes? Not many outlets in the UK but I have arthritic toes and bought a pair of her ankle boots for a wedding about four years ago. I was comfortable all day and have worn them quite a lot since. Not cheap - and some styles were .... well, a bit unusual...
Mine are definitely unusual but not peculiar! Lol.

I agree with Kate - shoe boots look great with a skirt/dress. I have some navy, black and a slate grey pair which I wear with matching opaque tights.

I often wear ankle boots with a knee length skirt, I also like what I call shoe boots. Like you I struggle with footwear having wide feet and the addition of a weak ankle following a break last year.
Believe it or not I’ve found primark really good for wide fit shoes (especially if it’s for an event, so I won’t wear v often).

Looking at the style articles, ankle boots can be worn with skirts every bit as much as with trousers.
Personally I don’t like seeing a gap of leg, but that’s just me! (My legs!)
Maybe coloured opaque tights to go with the outfit -or indeed as a contrast - and you will be very trendy!

I love glamorous shoes but unfortunately my days of wearing them are gone due to my troublesome feet. I wear ankle boots with a skirt. My favourite are shoe boots which look great with skirts and opaque tights in the winter. Good luck in your search.