I haven't read the article yet because I don't want it to influence my answer, although I have read some comments and get the gist.
Irina has a point re: our "eye" changes to adjust to fashion over time. I like that and can think of many examples such as women wearing pants instead of dresses or skirts being "risky." Also, "protest fashion" comes to mind: https://www.thecollector.com/h.....n-history/ for which some people were even jailed for taking sartorial risks. "Pushing the envelope" can make us, and others grow and change and I think that is a good thing.
However, back to the more lighthearted, red carpet risks, I agree it's subjective to what is "risky." I like bright colours and I wear them regularly, but some think it's a "risky" choice, particularly in a sea of black, grey and navy, but I don't mind and even get compliments.
As an aside, Rhianna's maternity clothing choices were very risky (or risqué), perhaps even shocking, yet so very interesting, wonderful and creative.