Honestly, give bald a try and get people's opinion. Being a guy means that it'll take 3 months for hair to grow back if you don't like it. It all depends on your looks. It's not necessarily a big buff guy look, either. Patrick Stewart was rocking the look for years - and yes, many women think he's good looking, even as he ages.
Take the leap. If it sucks, wear a hat. Seriously - It worked for Kenny Chesney.
I dated a guy who was going bald. While I'm not necessarily attracted to blad guys, he was a sweetheart! So, don't worry about it. As long as you're comfortable with who you are, you'll be OK. You could always keep your hair short.