So I recently had an issue of mod_rewrite not working on my mac osx after setting up my vhost and going through my httpd.conf and replacing all "override none" with "override all". So a couple of things that I learnt:

Firstly unless you going into System Prefernces -> Sharing and turn on Web Sharing OSX, apache will not read you httpd.conf or vhost file, it will just redirect everything to the folder /usr/htdocs (which didn’t even exist for me).

Secondly, you also need to change the file etc/apache2/users/USERNAME.conf to following.

<Directory "/Users/USERNAME/Sites/">
    Options Indexes MultiViews FollowSymlinks
    AllowOverride All
    Order allow,deny
    Allow from all
</Directory>