Using Classic Outlook on Windows for personal email, calendar, and contact management
There's only one good solution. Screw Outlook. They've deliberately downgraded it to the point they make you pay for 365, but frankly that's a downgrade too.
I went to Mozilla Thunderbird and can't believe how nice it is. And free. And it seamlessly picks up where you left off in Outlook, loads all your messages and contacts and calendar.