We understand many users are still preferring to stick in using outlook.com mail services (formerly popular known as Microsoft Hotmail, Livemail), they hold the mail accounts for more than decade, no strong reason to open a new gmail account just for the purpose of sending large files.
Microsoft does offer similar cloud storage services to their users, which is Microsoft OneDrive (former name as SkyDrive).
After logging in to outlook.com, users only required few simple steps to send out large files. Go to more setting,
After uploading, select the file
Share the file
Users can always add more than one recipients name
The share option can restrict recipients either view only or editable access
The final step is close the button and send out the document. To repeat sending same large files, users no longer need to reupload all files. Straight create a new message, then select share from OneDrive
Select and open the shared files
Finally, insert the mail message and send out