It takes a lot of time to delette the images from ticket, if there was for examlpe a letter mistake in naming. This function will be pretty usefull for designers, who are working with more than 50 images.
If you have JIRA Server (not Cloud), you can use the free Delete All Attachments plugin which lets you delete all the attachments at once on issues.
If you are on Cloud, unfortunately there is nothing that can be done. There are tickets open with Atlassian for implementing something like what you asked in your question - selection boxes for which attachments to delete. You can vote/watch these issues for both Server and Cloud:
Hey everyone! My name is Sarah Schuster, and I'm a Customer Success Manager in Atlassian specializing in Jira Software Cloud. Over the next few weeks I will be posting discussion topics (8 total) to ...
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