Boots suit anyone who's tired of checking the weather before deciding what to put on their feet, and anyone who wants one pair to see them through fetching the paper, a long walk, and whatever the evening turns into. If you have very narrow calves and hate any gap at the top of a knee high boot, or if you've got a foot that swells by the afternoon and you're eyeing something with a zip that's already tight in the shop, it's worth trying them on later in the day rather than first thing, and thinking twice before you commit.
Before you buy any pair, check a few small things while you're still standing in the shop rather than finding out at home. Walk a proper lap, not three steps, because heel slip only shows up after a bit of movement. Check where the top of an ankle boot actually sits against your leg, since a couple of centimetres either way changes whether it looks neat or cuts you off oddly. Bend your foot to see how stiff the sole is, because a boot that won't flex at all is going to be hard work on cobbles or stairs. If there's a zip, work it a few times, a stiff zip on day one tends to get worse, not better. And if you're between sizes, go up rather than down, since boots are one of the few things that get more uncomfortable with wear, not less. If you own none, start with a plain ankle boot in brown or black leather, low block heel, round toe, nothing with buckles or hardware to date it, because that's the one that goes under trousers and under a dress without you having to think about it twice.
Once you've got that pair, you'll find it goes into outfits you already have rather than ones you need to build around it. Jeans and a jumper, obviously, but also a plain midi skirt with thick tights, or a shirt dress you'd otherwise save for sandals weather, worn a season longer because the boots carry it. A mac over the top and it does the school run, the office, and a dinner afterwards without a change of shoes in a bag. It sits well under wide leg trousers too, just skimming the hem rather than disappearing under it.
The real pleasure, when you've got a good pair, is the sound and feel of a proper sole on a wet pavement, solid rather than slapping, and the moment you realise you walked the whole way there without once looking down to check your feet.
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