Do you have any strong feelings about messenger bags? Specifically, I am a bit torn between the north/south versus the east/west styles.
Unfortunately, we men do not have a lot of options available to us in when it comes to bags. Woman (as is usually the case) have a multitude of options for different situations, and in different colors to choose from. However, the one style rule that I always try to follow is function over form, and bags cannot escape this rule's graps. For school I use my incase laptop back pack:
It is functional enough to hold all of my essential gear (books and Macbook), but I don't look like I am going on a 8 day backpacking trip into the Andes. When I am lucky enough to travel I take my soft leather Rudsak brief case, but one bag that I do not have in my arsenal is a messenger. I am partial to the 'East/West' style of messenger bag in a simple canvas or leather:
However, if it is large enough (and does not look like a travel purse) I can't object to the 'North/West' style:
If you really have some courage, try a tote (WARNING: only for advanced users, or ALL Europeans):