"Pretty" vs "editorial"

I've been watching a lot of "editorial" tutorials lately in an attempt to improve my eyeshadow technique, and today I decided I wanted to try a daytime grunge-inspired eye. I also slept badly and my eyebags are huge, so I thought I'd just make them part of the look. I put on really minimal base, left my dark circles largely uncovered, and went to town with hazy eyeshadow, a heavy lower lashline and spiky lashes.

End result: I'm looking rather less "pretty" than usual -- I didn't do much to smooth or even out my skin, I'm wearing very little blush and I went for a matte lip which isn't my favourite finish -- but I actually quite like how it turned out, and it was fun to do my makeup without worrying too much about how nice or flattering it was (though I still think it's an improvement on my bare face). One of my coworkers even complimented my eye makeup today.

I always thought "editorial" basically meant "unwearable for most normal people", but now I'm really interested in trying other looks that I'd previously dismissed for being unflattering. I'm curious to hear from other people -- do you enjoy putting on less beautifying/less wearable looks?