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If it is in Dropbox, you can open from there using Share option. I think it needs to be (dual format) .mobi. Pick Kindle and Send To Kindle dialog will appear. You do not need to Save to Kindle Library, just have it sent to the device you are using.
Otherwise, if you have USB wire, and iTunes loaded, I think calibre is smart enough to find the Kindle storage folder that will be mounted. But it has probably been 8 years since I did any of this. The calibre documentation should cover this scenario.
Personally, I would use something other than the Kindle app for this side loading stuff. Convert to ePub and there are better options. I don’t have current knowledge of which apps to check out.
For me, Apple Books would suffice. You can just open from DropBox, and if you choose it will store in iCloud and sync between Apple devices. It’s also one of the few reading apps that has full Accessibility support (in particular Speak Screen, if you want TTS like function).
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