|$295/$275, Lo & Sons|
I'm really susceptible to "in the know" items. These are pieces that aren't super famous (e.g., Longchamps) but a certain echelon of professionals are all aware of. The Lo and Sons O.G. and O.M.G. bags are popular among fashion bloggers for being roomy, sleek and pretty much perfect.
Although I don't think I would carry this bag for day to day purposes, I would use it as a gym bag or as an overnight bag or as a larger carry-on for business trips (how profesh!). This is going to be a difficult decision though, should I go with the smaller O.M.G. or the larger O.G.? What color? (They have black, purple, and an army green). I recently purchased a new set of Tumi luggage, so I should probably choose a color that is complementary.