I am a petite woman - less than 5' tall. I purchased the Messenger bag last year and was very excited to try a new bag that was raved about by many DISers. I absolutely loved the bag & the organization ability it provided. But after a couple of days at WDW, I discovered it wasn't for me. First of all, when it got loaded (with not that heavy of stuff), it became too heavy for me. I don't believe the weight would have been a problem, but because all the weight was on one side of my body, the weight pulled on the shoulder that was holding the strap. Also, the weight caused the buckle not to stay in place, causing the strap to become too long. For me, I will go back to a small backpack - that way the weight will be evenly distributed across my back.