Check the drainage hole before you check anything else about an outdoor pot. Plenty look great on the showroom floor and then sit full of water after the first real storm, roots rot, and the plant you paid good money for is dead by the end of the season. A pot with a decent hole, or one you can drill yourself, is worth more than any glaze or finish. That said, once you get the drainage right, a good outdoor pot is one of the cheapest ways to make a patio look like someone actually lives there.
How a pot ages depends entirely on what it is made of, and this is where I'd slow down and actually think. Terracotta breathes nicely for the plant but it is porous, so it soaks up water, and anywhere that freezes hard in winter, that water expands and the pot cracks. Fine in Phoenix, a gamble in Cleveland. Glazed ceramic holds up better to cold but can craze and chip if it gets knocked around, and a chip on a glazed pot only gets worse, it never heals itself. Concrete and fiber clay composites are the ones that just shrug through the seasons, they get a little weathered looking, maybe some pale patches where the sun hits hardest, but they do not crack or sag. Plastic and resin pots are the budget option and some of them are genuinely fine, but the cheap ones go brittle and chalky within a couple of summers and the color fades fast, especially anything dark. Wipe pots down a couple times a year, bring anything delicate in before a hard freeze, and most of them will outlast the plants you put in them.
The difference between a pot that lasts and one that disappoints usually comes down to wall thickness and the base. Thin walled pots crack at the rim first, that is the weak point, so run a finger around the edge and feel for anywhere it is thinner than the rest. A heavy, even base means the pot will not tip in wind, which matters more than people expect once you put a top heavy plant in something narrow. Good drainage holes are molded in, not an afterthought stamped on later, and a pot with a slight taper rather than straight sides will let root bound plants slide out without a fight when it is time to repot.
On delivery day, tip the pot and look inside for cracks near the base, run your hand around the rim for rough spots, and set it on a hard surface to see if it rocks. Small things, but they are the ones that turn into a mess six months in.
Is this pot going to survive a winter I haven't had yet, or just the nice afternoon I bought it on?
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