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What's actually different about holiday clothes, versus just packing your normal stuff in a smaller bag? Mostly it's fabric and colour, not cut. The same shirt shape works everywhere, but one version is woven to breathe and dry fast and the other just sits there going damp against you by eleven in the morning.
In the shop, get your hands on things before anything else. Linen and linen blends should feel slightly rough and a bit papery when it's dry, that's normal and it softens with wear, but if it feels waxy or stiff in a way that doesn't give, it's probably got too much synthetic mixed in to actually keep you cool. Check buttons on shirts are sewn through properly rather than glued, because that's the first thing to go on a cheap holiday shirt, usually around day four, usually right as you're about to go out. Shorts and swim shorts need a proper check of the drawstring and the pockets, a mesh lining that doesn't bunch, and enough room through the thigh that you're not doing an awkward shuffle walk on sand. For anything linen, hold it up to the light and have a quick scan for weak patches near the seams, cheaper weaves can be uneven and it shows there first. Colour wise, lighter shades genuinely do keep you cooler and show salt and suncream marks less than you'd expect, while anything dark cotton will look fine in the shop and faintly tragic by the pool.
Over a week away these clothes take a battering that your normal wardrobe never does, suncream, pool chlorine, sweat, sand worked into every seam, so wash things properly when you're back rather than just airing them out, and avoid the tumble dryer on linen if you want it to keep its shape rather than shrink into something that fits a smaller man. Fit is where most men get holiday clothes wrong, buying a size down because the fabric feels thin, then it clings the second you're not dry. Shirts should hang loose enough to move air through them, shorts should sit comfortably on the waist without a belt doing all the work, and anything with elastic should still look like it fits when it's wet, not just when it's fresh out of the packet. Watch for sleeves and hems that look fine standing still in a changing room but ride up the second you lift your arms or sit down.
After one proper trip the colour softens a shade, the linen relaxes into creases that stop looking like mistakes, and the whole lot starts looking like it's actually been somewhere rather than straight off a shelf.
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