A bloke's perspective: 6/10 for planning, 1/10 for execution. The problem - in my eyes at least - is that it doesn't look intentional or deliberate, rather it looks as if he's stopped taking pride in his appearance for whatever reason or is having a "I've lost my razor sir" moment. If he had a neat line across the bottom and took the hair off his neck it'd look much smarter and squared away, and like it's a deliberate decision to look like that rather then a lack of action.
I say this with the caveat that my DW buys all my clothes for me (or chooses what to buy rather) as left to my own devices I'd still be cutting about in purple t-shirt, blue jeans, desert wellies with green paracord laces and a nylon bomber jacket on the basis that it worked the first time I was 17 and the second time I was 17 so why not the third? Eh, er... I'll see myself out..