Can you actually walk in a heeled boot, properly walk, not totter from the taxi to the door? Yes, if the heel is the right shape. A block or a stacked cone heel under two and a half inches does everything a stiletto promises and none of what it threatens. That's the whole decision, really, before you even get to colour or leather.
These earn their place from the first cold snap right through to the bit of spring where it's still too raw for bare ankles. They're brilliant for anything that sits between dressed up and dressed down, a lunch that might turn into a few more hours than planned, a wedding where you need height but can't be seen clinging to someone's arm on cobbles. I wouldn't reach for them for a long day on your feet, there's a limit, but for an evening where you're mostly sitting, standing, moving between rooms, they carry you further than you'd expect. Mine have done train platforms, a wet car park, and one memorable dash across a market square, and the heel has never once felt like it was about to go.
They sit well against most of what's already hanging up. A straight leg trouser tucked just so, a midi skirt that skims the top of the boot rather than fighting it, even a plain dress that needed a bit more edge than a flat shoe gives it. I had a bucket of deep burgundy ranunculus on the counter last week next to a stack of grey green foliage, and that's exactly the pairing a good heeled boot does for an outfit, it's the thing that makes everything else look like it was chosen on purpose rather than grabbed in the dark. A brown or black pair takes you furthest for the least thought, but don't write off a deep wine or a bottle green, they do the same job and look far less ordinary doing it.
If you've none at all, start with a plain leather ankle boot in a block heel, in black or a good dark brown, nothing with a buckle or a zip detail you'll tire of by March. Check the heel after a winter of pavements, a decent one barely scuffs, a poor one shows the glue line within a month. The small pleasure, the bit that makes a good pair worth having, is the sound. A proper heel on a quiet street has a bit of a click to it, and there's something about that sound that makes you stand up straighter without even trying.