There's nothing uglier than paint peeling off, part rust showing through, and age written all over it.
If all else fails, throw it in the bonfire and burn all the paint off. The heft of this plant stand lets me know that it's sturdy and built to last, so it's worth refurbishing to make it usable again.
Some people are shocked that I don't plan on painting these kinds of things again. Why would I go to the trouble of removing all the paint, just to cover it all up again. Rust is king, and my style.
A few times around in the fire, and then it's time to age the exposed metal. There are several ways to do this, depending partly on the time of year.
In winter, if I burn the paint off something, a few months out in the elements, getting rained on is enough to add some patina. Occasionally, to hurry things up, I'll spray the burnt object with some straight bleach, which brings on the rust.
This one might need another shot in the fire, to completely melt off the paint and burn it. Move it around a lot with a pitchfork to get it from all sides. Steel wool or a wire brush will take off any left over bits, or soot.
This plant stand came to me originally with a scraggly spider plant in it, which I renovated and replanted in a better pot. In a few months, the combination will look fabulous.
Later; the plant stand with the accompanying spider plant have spent the summer out in the elements, and both look better for it!