Help finding winter boots

I am looking for boots that pair well with cropped and slightly flared jeans - think Mother’s Hustler Ankle Fray or similar. I have a few pair of ankle boots, but they all seem to hit below the denim and then look a bit weird/show too much skin for a cold day in Toronto (where I’m based). Please help!

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Hello!
Are you thinking flat or heeled boots?
I have those exact Mother jeans, I wear them so much with a pair of Chelsea boots very similar to these from & Other Stories and find they hit just at the right height.

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