What a great question! I'm very restless when it comes to my hair and like to play around with any variable I can control without dye/product/heat styling. Basically: length, bangs, part, layers, texture to a certain degree. I do a lot of chopping and growing out. Looking back at photos from five or six years ago, I think the hair that felt just right to me in the past would feel a bit too classic, crisp and controlled for my current style direction. (See side-by-side of Spring 2016 and today for comparison.)
I have pretty well-behaved hair that I can nudge in one direction or another, and I tend to like it better when I do less to it. I dislike overly styled looks and have no patience for "doing" my hair each day. I enjoy pixies but always let them get shaggy; the constant maintenance trims are too much for me. Similarly with blunt-cut bangs, I love them but get tired of maintaining them, so I end up taking lots of breaks from them and have gotten somewhat okay at the grow-out phase. All of this to say, my hair is probably more a reflection of my personality than anything else: I demand low-maintenance, but crave variety. Granted, those criteria drive how I dress as well.
Your salt-and-pepper hair is really gorgeous, Irina (I'll be your twin in a few more years!). I could certainly picture you in a pixie if you wanted to go that direction, or with a shorter bob. You might ask your hairdresser about how to add a little edginess to a classic bob. Graduated in the back, undercut on the side or back, asymmetry, bangs...
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