I found a way without paid software (rar) and without the inconvenience of Dropbox:
1) Use 7-Zip
2) Right-click on the file / folder to compress; select 7-Zip -> Add to archive
3) Save as .7z with password
4) Right-click on the newly created .7z file and zip it normally as .zip
Since .7z file is password protected, Gmail needs to know the password in order to know the contents, including file extensions. So, it cannot block it based on the contents.
Hope that helps.
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