Hey guys (& girls), I'm a loyal backpack user and have been throughout my life. I've never owned or used a messenger bag, but I'm considering purchasing one to use casually for work or during times when I have to look presentable (ie. suit jacket, and/or shirt and tie). I wouldn't really classify myself as a metrosexual but I do care about my appearance and want a product that reflects that. Also, I'm a recent college grad and want something that I can take with me to job interviews and to business meetings/trips in the future when I finally land that "grown-up" job (currently working at Abercrombie & Fitch as a sales associate). Basically, what it boils down to is I need something more professional but I don't want a full-blown briefcase. Since I'm a younger professional, I want something a little different, a little more trendy compared to the briefcase look. Ideally, I want something that is smaller in size (not too big because I'm a smaller guy at 5' 7", 130lbs)...it needs to hold my 13" MBP and a book/notebooks along with a couple of files and macbook charger. Pretty simple - just the basics to tote to and from work or school essentials if/when I go to law or grad school. I searched the forums and did some research online and was able to find at least 2 bags that I'm interested in: - Graduate by Far Horizon Traders - EW Messenger - Jackson by Fossil What do you guys think? They both look like they would suit my needs pretty well but what's your input? Do you like one over the other or is there something else that I should consider? What do you think of the whole "man bag" thing in general? In business class, they tell you that your education is to prepare you for the real world so you can go from backpack to briefcase. I appreciate your $0.02!