If you use any type of smartphone running Windows Mobile or similar, it shouldn't be too difficult to get Outlook synced up via a USB cable. The Moto Q, Samsungs and Treo Centro should be fine. Though I've never tried it w/ a non-PDA phone.

Blackberries and iPhones also connect, though some may require an extra app. I've used a Treo w/ Outlook so that's not an issue either.