Court shoes have a reputation for being the sensible choice, the thing you buy for an interview or a funeral and then resent for years. I think that reputation is mostly earned by bad ones. A good pair earns actual affection, the kind where you reach for them without thinking, but you have to get past a lot of stiff, shiny, badly shaped ones to find it.
The difference shows up in the first five minutes of wearing them, not on the shelf. Cheap courts are usually a thin synthetic upper over very little padding, with a seam that sits right where your foot bends, so they crease and crack within a season. A well made pair has a softer leather or a proper suede that gives slightly at the toe box, a heel that's set so your weight lands centred rather than tipping you forward, and a lining that doesn't feel like cardboard by midafternoon. Check the stitching round the topline too, if it's wavy or the glue's visible, that's a shoe that'll separate at the sole within a year of regular wear.
Where they struggle is anywhere casual tries to meet them halfway. A court shoe with a floaty sundress or wide linen trousers looks like you got dressed by committee, half office and half holiday. They want structure around them, a tailored trouser, a pencil skirt, a coat with a proper shoulder, not anything slouchy or sporty. Trainers live in one world and courts live in another, and the clothes in between need to pick a side.
Fit is where most people go wrong twice before they get it right, me included. Courts should feel snug across the widest part of your foot with almost no gap at the heel, because there's no lace or strap to make up the difference once the leather stretches. Buy them too roomy thinking you need toe space and you'll be sliding forward into the point within a week, which is how you end up with bruised toes and a shoe that looks a half size too big. Buy them too tight and they'll never truly soften, whatever anyone tells you about breaking leather in. A slightly higher vamp also keeps heels from gaping at the sides, which is the detail nobody mentions until they're stood there with daylight showing down the side of their foot.
They're a poor choice for anything involving real distance on foot, wet pavements, or a day where you're on your feet more than you're sat down. Rain gets into a pointed toe fast, and most heel heights on a court aren't built for cobbles or long station walks. For a desk, a meeting, a lunch, they're exactly right. For a day that's mostly movement, they're the wrong tool, however good the pair.
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