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Pruning overgrown Osmanthus to shape
Our Osmanthus has grown massive over the last two years and I wanted to bring it back to its original parashute shape .
Should I start with pruning the lower branches after late summer autumn flowering ?
My Gardener thinks it should be ok with a heavy prune but I read otherwise.

Should I start with pruning the lower branches after late summer autumn flowering ?
My Gardener thinks it should be ok with a heavy prune but I read otherwise.

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"Have nothing in your garden that you don't know to be useful, or believe to be beautiful."
Taking off the lower branches would change the shape quite a bit, and leave bare trunks, if I'm understanding what you were planning to do.
I live in west central Scotland - not where that photo is...
Yes I would like to take off the lower branches and bring it close to its shape when I bought it - see below .
Then to reduce its high I would like to reduce hight as well.
Flowering is in August so I am thinking of doing this in before winter.
Prune soon after flowering.
Prune to a shape that you like.
"Have nothing in your garden that you don't know to be useful, or believe to be beautiful."
As far as the canopy is concerned, you can take some individual branches out - quite far back, and again - stand back and check as you do it.
That will reduce the height, but will leave a looser shape overall, which is usually much nicer than just shearing everything off and leaving it looking like a toadstool/pudding. You can then go back at a later date, or next year, and do some small adjustments, or take more branches right out, depending on how it looks and how satisfied you are with the result.
I live in west central Scotland - not where that photo is...