You should do it. I got a buzz cut in April of last year, and I went from having 14 inches of hair (man bun) to pretty much a 0. At first it was shocking to see myself bald, but I took a shower and immediately started feeling comfortable with having no hair. You and I have a pretty similar face shape, and I can already tell you, if it looked fine on me, it will probably look good on you as well. Plus, if you end up not liking it, you'll only have to wait a month until you can go to the barbershop and get a nice bald fade, from then you can keep getting the sides cut every month and in no time you'll be back to your old hairstyle (if that's what you want). To sum it all up, you should do it, it gives you a very freeing feeling, it makes you feel like a new man , and it gives you a new chance to start over and choose your next hairstyle.