It is possible with the attachment macro, but only when you use the browse option. In the macro settings you define the labels you want to filter by, and allow upload. Note that the labels have to exist already. When you upload files they automatically get the labels.
There are open issues on the drag and drop feature:
I was hoping to find a solution here. We want to use macro's like content by label, recently updated, livesearch to find content, but can't really use those because not all content is found when users drag and drop files. So hopefully this will get fixed soon! Please vote for the issues!
(We are using Confluence Server 5.7)
I do not think this is possible with standard macro, but you can develop your custom listener (https://developer.atlassian.com/display/CONFDEV/Event+Listener+Module) and catch for https://docs.atlassian.com/confluence/latest/com/atlassian/confluence/event/events/content/attachment/AttachmentCreateEvent.html events (and label attachments as you need)
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