I have the same problem with boots, I want to get some so I don't get wet/dirty trouser hems every time I go outside, but don't know what to wear with them. I only like bootcut or wide-leg jeans and trousers, that's the only style I've ever worn since I was a teenager, and am sure 'skinnies' would look horribly unflattering on me, I just can't even think about wearing them.
For walking the dog in snow/slush I've been wearing hiking boots with waterproof overtrousers, but that's obviously not appropriate for all situations!
Maybe I'll try on some straight-leg trousers sometime, I just have such a big mental block when it comes to doing so
I hear you about the wet hem, it's a nightmare! I have mid calf boots and have been wearing boot cut and straight trousers with a wool knee length sock or leg warmers over them, it keeps any size of hem inside the boot and you can take them off when you get to work and just wear the trousers over the boot. I haven't tried, but would love to get some thigh length socks, they keep your legs so warm. Starting to get a bit of a leg warmer thing now! [oh dear] Should add am already wearing tights under my trousers.