Originally Posted by
Quanty Custom files shouldn't require you to re-install CSS (might be wrong).
I had a similar issue when I used to play on my school computer (dark, dark times) I would suggest just going into your cstrike folder and maybe placing your download folder somewhere else and reconnect to the relative server, it should recreate the folder and re-download whatever the server is using but by the sounds of it might be an issue with the skins.
If that doesn't work you can just put all your custom files back into the cstrike folder and replace the new one and it will just revert it back to before so no harm done if that isnt the issue ^.^!.