I was really worried about not looking cute and looking too “tough” since I started buzzing off all my hair due to baldness. But I think it’s been ok. I wear dark thick framed glasses, and a lot of light or pastel colored clothes. I keep a VERY short beard, just to give me some fuzz and distract away from my head. And I smile a lot.
I’ve also started shopping for cute hats. It’s been tricky to find hat styles that I really like, but I’ve found some cute ones.