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If you don't like the date format Outlook uses on screen or in printouts, you need to change the long date format set in Windows Control panel, Regional settings.
Note, the day of the week format is controlled by the width of the Window on screen, the month, year and date are customizable.

Open Windows Control panel, Regional and Language settings. Today's date is shown using the long date format setting. To change it, click the Customize button next to the language selection. Select the Date tab then select a new long date format. If the date format you want to use in not listed in the drop down, type it in.

Valid day/date codes listed below; valid date separators include comma, period, and dash. If you enter a character that is not supported, Windows will either tell you or the sample format on the dialog won't change after you hit Apply. Note that any changes you make will apply in all applications, not just Outlook.
Day of week: ddd or dddd (Sun or Sunday)
Month name: M, MM, MMM, or MMMM (1, 01, Jan or January)
Date: d or dd (1 or 01)
Year: yy or yyyy (10 or 2010)
Separators: dash, comma, period (possibly others)
Updated Monday February 01 2010