Although the NTFS or FAT32 file systems can support filenames up to 255 characters, it isn't possible to use a file input to upload a file with a name that long. This is due to the way that IE inserts the chosen file into the form field.
When you browse to a file and select it using the File input, IE inserts the full file path. IE also limits you to 255 characters, but counts the file path against that limit. This means that if you had a path with a length of 55 characters, the maximum length of the file name that you could choose to upload would be 200 characters.
In order to avoid this limitation, you should use a non-IE browser or a client side tool like JFile or XFile to choose and upload files. The only limitations on filenames these tools experience are those implemented by the file system.