I’ve never seen a guy look cool wearing them, and I don’t know a single woman who owns a pair.
You may look like a huge nerd wearing them, but the experience of hiking in Vibram Five Finger shoes is ridiculously cool.
You can feel the texture of the ground beneath your feet without any of the negative side-effects of going full-on naked barefoot.
You can feel the sand but not the heat, the pine needles but none of the poke.
The only thing to keep in mind is that your toes are actually separated, so you can easily 1.) stub a toe, 2.) accidentally get your trekking poles stuck between your toes, and 3.) find small objects lodged in strange places. (photo below)
In hiking boots your foot stays mostly flat against a hard sole. In these shoes you use muscles in your legs and feet that you likely haven’t flexed since you were a kid.
Give them a try, but make sure to wear socks. (yes they have to be toe-socks)