Not bad but why are you shaving off your sides? If you're going to do that, why not just completely shave your head? Leaving the patch of hair at top with the sides shaved off is not much better than simple bowl cut. For your 2nd attempt at DIY, it's not bad. It's better than what I could do. And you pull off "I'm cool and don't give a shit what you think" look just fine. But if I was in your situation, I would start paying for haircuts again or get the wife to start cutting the hair. My wife cuts my hair and have for over 10 years now. She's not good as the ladies at the professional hair salon but she's way better than people at places like Great Clips or any of the chain haircut places. The only time I pay for haircut is when I'm traveling in Asia. I visit and pay the ladies at hair salons there because they're really good at cutting my hair and they give you the total salon treatment from washing your hair, massage, and styling. I feel good and fancy when I leave those places. All other times, my wife cuts my hair at home.
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