Bald head?

I was leaving a CVS near my job when I overheard two of the young employees discussing a woman who had just left. I never saw the women, but the convo sounded something like this:

"but she was pretty" the girl was saying.
The guy said "No, she was bald, I can't do bald headed women. ur just saying that cause I don't like it."
"I was thinking she was pretty before you even said anything! What about Amber rose? Shes a model!"
He said "but she got money- to make herself look good without hair. A regular chick can't do that. Then she just bald"
*laughter from other male employees*

I was like wow. I had just read a blog post about transitioning and going to short hair, which is often an issue I contemplate when giving transitioners advice. It's hard imagining not having any hair, for a few months, or maybe longer depending on how one chooses to wear it. Granted, most of the time the big chop does not = completely bald, but it is still a shock. Will you like it, will guys like it, will your mama like it? Is it worth it? I still say YES, but I hear conversations like this and can't help but to sympathise with the women who imagine this conversation when deciding to wear wigs, or braids or weaves, or just never go for the gusto and BC.

So I went home trying to think of some other "bald headed" women who are rocking it, and exemplify the freedom that short hair brings. I immediately thought of Zhane, Alek Wek , and Grace Jones. My boyfriend thew in Noemie Lenior. Then I got stuck. I did searches... I was stumped. I see lovely ladies on the street rocking the close crop all the time, but how do I share their confidence with a transitioner? Advice?