I filled my pot with rubbish - old compost, gravel, broken slate etc to the required depth and then put a plastic pot inside and planted it up with the variegated vinca. Good drainage and the pot stood upright through the gales we had earlier this year.
I have this campanula which is in a large round plastic container which just fits and rests on the top of the chimney pot. It has been in there for years now and never lets me down. It is removable from the chimney pot if needs be.
Re the chimney pot in the first picture: I would turn it upside down to stop the soil washing away in the 'flutes'. If turned they would be like bowls and hold soil and moisture better.
Thanks we left it there as it was v heavy, was wondering which way it went.
Like @Uff my chimney pot has a Vinca planted in a pot. The trick is to find a plastic pot that fits securely, but not so tight that you can't get it out if you need to.
@davebettz. Thank you for your comment. The chimney pot is empty and just holds the plastic container in place. Goodness knows how it has survived all these years. It is green all winter and comes to life in Spring. A good watering and a feed now and again and it rewards you. I think this is it's best year yet.
Try Erigeron karvinskianus in one of your pots. It prefers full sun but is just as happy in light shade. It flowers non stop from May to December and is perennial. It has a pleasing cascading habit as it gets larger and will look great at that height!
Just seen @BenCotto's post - you've got two votes for that plant now!
I had a Persicaria runcinata 'Purple Fantasy' in mine for a while, in a plastic pot that fitted inside and with a saucer inside the bottom of the pot as they don't like to dry out. It looked pretty good but needed a lot of watering and it's a herbaceous plants so there was nothing there in the winter. This year I've replaced it with a prostrate rosemary (and no saucer) which is just starting to trail and I think it's going to work well.
'If you have a garden and a library, you have everything you need.'
Some people fill the chimney pot with soil and treat it like a baseless pot, which I would like to try one day. Some just put a pot in the top, which I do at the moment, because I have a narrow garden and want to move the chimney pots around all the time - out of the way.
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Just seen @BenCotto's post - you've got two votes for that plant now!
This year I've replaced it with a prostrate rosemary (and no saucer) which is just starting to trail and I think it's going to work well.