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The phrase "with his" is correct and usable in written English.
It is generally used to indicate possession or accompaniment. For example: Tom brought his dog with him along to the park.
Exact(60)
With his baseball cap.
With his foot.
With his little blindfolds?
Start with his family.
Start with his feet.
With his Jun.
Him with his family.
Thoughts with his family.
With his penis.
with his two children.
Off with his head!
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com