Coach store post look a lot like a purse?" Answer: You have a good point, and while there's no one thing that makes a bag more or less masculine, there are a few parameters that taken collectively make all the difference. In order of importance:
You want this thing to be at least as big as the briefcase it replaces. Your bag should look like it might contain a full-sized laptop computer, a leather-bound notebook, a hard sunglasses case, a flask, a sidearm with an extra ammo clip, and possibly a motorcycle helmet.The dimensions are not the only factor, but if it looks like all you might have in there is an iPad—or any other kind of pad, for that matter—there is no hope.
2. Aspect Ratio
It has to be wider than it is tall. No exceptions.
3. Carrying Method
Safest bet is a pair of padded handles, as on a soft briefcase or tote, which requires you to make a fist while carrying it. Next up would be a same-side shoulder strap, as seen on the classic messenger bag, and the wider and more utilitarian the better. Use a cross-body strap only with extreme care, and only if the bag is so large and heavy that you'd walk with a list otherwise.
Generally speaking, you want darker and more neutral. Black and deep brown are safe. Medium brown or cordovan is pushing it. Anything lighter than that had better be a battered-to-s**t canvas work bag that no self-respecting woman would ever be seen carrying.
Check our handy chart above, showing examples from both ends of the male-appropriateness scale. And yes, that Gucci bag was in fact found in the men's section at Bluefly.