I saw something like this on r/malefashionadvice but they would mail you a box of stuff every month and you would just keep what you liked and mail back what didn't fit or you didn't want. looks like a few sites are doing it now

http://www.reddit.com/r/malefashionadvice/comments/gyg6z/i_g...

https://www.trunkclub.com/

http://www.frankandoak.com/

http://www.manpacks.com/