The thing nobody tells you about leather trainers is that they look mediocre for the first fortnight and then suddenly, somewhere around wear fifteen, the leather softens at the crease and stops looking like a box fresh photo and starts looking like something you actually own. Mine took about three weeks of proper walking, not just shuffling round the house, before the toe stopped looking stiff and started moving with my foot instead of against it.
If you've got none, start plain. White or a pale neutral, a simple low top shape with minimal stitching detail, because that's the version you can wear with everything while you work out whether you even like the silhouette on you. Skip the chunky sole and the mesh panels until you know. On sizing, go true to your usual size but check the toe box specifically, leather doesn't give the way canvas does in the first few weeks, so if your toes are pressing on day one they'll still be pressing on day thirty, it won't magically stretch to save you. The usual fit problems are heel slip in a shape that's too narrow at the back and a crease that digs in across the top of the foot if you've gone half a size down thinking leather needs room to grow into. It doesn't, not really. Buy for now, not for hope.
On colour, white is the easiest to live with in theory and the hardest in practice unless you're willing to clean it, so if you want low effort go for a stone, tan or soft grey instead, scuffs just read as character rather than as a problem that needs addressing. A true white pair is lovely for about six weeks of careful wear and then becomes a project. Matte finishes hide more than anything with a sheen, which looks sharp in a shop and shows every mark within a day outside it.
These sit happily under straight leg jeans, with a midi skirt in the warmer months, and with plain trousers for anything that needs to look a bit put together without trying. They struggle in proper rain, leather and puddles are not friends, so they're really a spring to early autumn shoe rather than a year round one, and I'd keep something synthetic or suede for the genuinely wet weeks.
Put a pair with the jeans you already wear to death and they quietly make the whole outfit look like you dressed on purpose, not like you grabbed whatever was by the door.