To me, messenger bags have always been synonymous with mailmen and Dan Humphrey. Now don't get me wrong, I appreciate both of these fine specimen (in different ways, of course) but I never aspired to emulate their style. Lately though I've seen myself pining for one of these cross body contraptions. They just seem much less troublesome than the standard oversized/leather/satchel bag. As someone who lugs around handbags that weigh almost as much as a Kindergarten class, handbags always seem to be a hindrance rather than a tool of efficency . I always seem to be knocking someone in the elbow with the back of my bag. And let me tell you, it's not easy squeezing into small spaces with a bag the width of a tree trunk.
This handbag history is probably what lead me to think that there is something quite liberating about being hands free, about not having a huge burden on your shoulder (literally). The messenger bag in it's utilitarian aesthetic really captures the meaning of the quote "Wear the clothes, don't let them wear you." Well, I'll certainly be wearing one sometime soon.