In Outlook 2007 after you have attached your picture as a file (and not when inserted as an image in the body) you can press the little expand arrow in the right bottom corner of the Include section. This will show you the Attachment Options pane which allows you to resize the picture.
In Outlook 2010 this option can be found in under the File menu, once the image(s) are attached to the e-mail.
File - Info - option: Resize large images when I send this message.
In Outlook 2010 you can no longer choose between different sizes but the image will be resized proportionally so it won’t be larger than 1024×786 pixels.