I was actually asked this question last Saturday. The inquiring person were slightly influenced of wine (like that would have mattered). As I also was slightly under the influence, my first response was a smart ass “Of course (or similar, I can not really remember, but a cocky reply it was).
The reply was followed by a giggle, the kind only “under the influence women” can do.
The giggle came from the fact that I do not see me as cool at all. Cool people are the ones who wear hats or dresses with polka dot stockings. I don’t.
But it might be so that I have both well grounded self-esteem and self-confidence, so to answer the question: “No, this has not always been the case.”
By the way, I just read the heading of this blog post to my husband. His reply was: “You? Cool?!”