What shoes do you wear with various outfits, at 50?

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I'm in a flux!
Cannot figure out what shoes to wear with each 'look' anymore ..
Can I ask what do you wear with jeans/ jumper combo
Or what boots with dresses/ jeans for work.
I feel so frumpy lately.. 5'7
I've lost my shoe mojo and need inspiration please!

I had this dilemma last year and realised it was because I was still wearing skinny jeans/trousers and nothing looked right anymore, apart from knee high boots. I switched to slim and tapered styles and wear them either cropped slightly or rolled up with ankle boots. If you get boots which go up the leg a bit then you don't get cold. I have three pairs of ankle boots, all of which do for smart casual.

I also have a pair of warm trainers from Mango, there are loads around in this sort of style https://shop.mango.com/gb/women/shoes-leather/leather-panel-sneakers_57084417.html.

I have a few ballerina type shoes but would only wear those to parties/inside at the moment as it's too cold.

I am 48 and i wear mom jeans or midi skirts/dresses - I wear black Solovair monkey boots with everything. They replace my previous ones which were DMs. If I want to wear heels I have a very old pair of very classic knee-high boots from M&S and a pair of very high black velvet platform sandals from Hobbs. All quite classic looks. I wear 100 denier black tights.

I think a lot depends on whether you have good legs (I don’t) and whether you like to try different looks, especially skirt lengths and trouser shapes (I don’t).

In winter I wear biker boots or chunky-soled Chelsea boots with jeans, wide-legged culottes and some midi skirts. I also have a couple of pairs of these dullish but useful M and S blocked-heeled black ankle boots to wear with black tights and dresses and more pencil-type skirts.
https://www.marksandspencer.com/ie/block-heel-sock-boots/p/clp60610572#intid=plpnav_pid_pg1pip48g4r7c4&gid=1&pid=2