The 'upgrade' from Hotmail to Outlook was officially completed in April 2013, so you seem to be behind the times!
Howver, any 'upgrade' from Microsoft inevitably means that simple tasks are made far harder. I suggest forgetting about Hotmail/Outlook altogether and swithing to a decent, reliable and intuitive email service:
http://www.gmx.co.uk/
(By using the 'Mail Collector' facility you can get mail sent to your old Hotmail/Outlook address automatically forwarded to your new GMX one, so the transition is really easy).