The mistake is assuming a white shirt is a white shirt, and buying on the strength of a good collar alone. The fabric underneath that collar is doing all the actual work, and a thin, slightly shiny cotton will look crisp for exactly one wear before it creases like a shopping receipt and goes see through under any decent light. Specifically, the most unflattering thing on earth.
A good one earns its keep over months rather than days, so judge it on that timescale, not the first Monday out of the bag. Proper cotton poplin softens slightly with washing but keeps its structure at the collar and cuff for years if you treat it kindly, which mostly means not tumble drying it to death and ironing it while it's still a bit damp rather than bone dry. The buttons matter more than people expect, cheap ones go dull and yellowish long before the fabric does, and that's usually what makes a shirt look tired rather than any actual wear on the cloth. Whites also show their age unevenly, the body stays bright while the underarms and collar edge grey off first, so a shirt that washes at forty rather than needing a boil wash will simply last longer looking the way you bought it.
Before you buy, hold it up to a window if you can. Thin cotton is instantly obvious that way, and it's the single detail that separates a shirt that reads expensive from one that reads cheap, regardless of what either actually cost. Check the stitching at the buttonholes, and check that the shirt has proper interfacing in the collar rather than something floppy that will roll over by lunchtime. A shirt with no give at all across the back and shoulders will fight you all day, so a touch of elastane in an otherwise good cotton isn't a sign of weakness.
Where a white shirt genuinely isn't the answer is anything involving red wine, tomato based lunches, or small children with felt tips, obviously, but also anything that needs to go twelve hours without a single crease, because even good cotton will show a day's living on it by evening. If that's what you need, you want a shirt with some synthetic content in the mix, and you should stop expecting pure cotton to behave like armour. On shade, true white is the hardest to keep looking fresh and the first to go grey in a mixed wash, so if you only want to own one, go slightly off it, towards ivory or a soft ecru, which hides a multitude of sins and still reads as a white shirt from across a room.
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