I think all the bags in the GQ article are ugly as heck and don't look comfortable at all. I also don't particularly see a point of carrying a bag that small. If I'm going to carry a bag, it's because I need to carry something that doesn't fit in my pockets. I can't think of anything I would want to carry that would need to be small enough to fit in that bag but so large that it doesn't fit in my pockets.
I like bags a lot. But in terms of daily utility, given the amount of flexibility that exists in the typical male wardrobe, there is absolutely no need for me to carry a bag unless I'm carrying around a laptop or tablet. All of my pockets have something in them, but they don't look bulky, they're not uncomfortable, and I don't feel weighed down by them.
I don't think carrying a bag like the one pictured in the second article would make you stand out as a guy in normal everyday life. I do think you would stand out if you carried one like in the GQ article. BUT - if that's what you like, that's what you like. Confidence is key in pulling off most wardrobe or accessory choices. So just own it.