I spent years thinking heeled sandals were a summer dress problem to solve, so I bought them to match one outfit and then wondered why they sat in a box for eleven months. What fixed it was buying a pair in a colour that had nothing to do with any specific dress at all, a sort of biscuit tan that goes with everything and nothing in particular, and suddenly they were on my feet every week from May onwards.
The thing nobody tells you about cheap heeled sandals is that it is never the heel that fails first, it is the footbed, because a thin, flat strip of unpadded leatherette with no give in it will have you hobbling by the time you reach the second drink or the second meeting, and the straps on the bad ones tend to be stiff enough to cut a line across the top of your foot that stays red for a day after. A better pair has a bit of padding or a contoured sole you can actually feel underfoot, and straps with some flexibility in the material so they move with your foot rather than fighting it. Where they let you down badly is pairing with anything already busy on top, a printed dress or a textured bag, because a heeled sandal with any detail of its own, a knot, a woven strap, a bit of hardware, wants a plainer canvas to sit against, otherwise your whole outfit is shouting at once. They are also, whatever the shop lighting suggests, not a cobblestone or a wet grass shoe, and I learned that the hard way at an outdoor wedding where I spent the reception walking on the balls of my feet like I was auditioning for something.
Where they genuinely earn a place is anywhere with a dry, flat floor and a reason to dress slightly up, a dinner, an afternoon that turns into an evening, a work thing with drinks after, and they carry a plain midi dress or wide leg trousers better than almost anything else in the warmer months because the ankle stays visible and the whole look lengthens. Come fog and pavement puddles I put them away, because a wet strap against bare skin in October is a specific kind of miserable, and no heel height is worth that. I would also say, honestly, go lower than you think if you are on your feet more than an hour, a block or a slightly wider heel has saved me more evenings than a thin stiletto ever has.
Next time you are holding a pair up, check the footbed with your thumb before anything else, if it gives even slightly, that is the one to try on.
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