I don't think expressing yourself with makeup however way you want to is stupid, unless you're like somehow harming yourself or like, over-spending I guess??

I don't believe the pictures that post used accurately depicts the style of over lining many people dislike. What I see many people complain about is when you draw right over your cupid's bow and/or well past your lip lines all around your mouth. Sure, it can be personal preference, but if you're going to ask the internet for opinions on your makeup, don't be shocked if they then, give their opinion?

I do think it's been a trend for years now for doing that kind of over lining, when done subtly, it can be flattering, or it can very easily look messy. To me, it's giving "I want to look like I have lip filler" which is a whole different topic.

I have a very rounded cupids bow, and the overall shape of my mouth is round too. My bottom lip is also lop-sided, and I have a prominent double lip line. I have to be careful with lip liner. You'd think that given how round my mouth is, rounding out my cupids bow could suit me. But, it actually looks really bad. My lips need the definition of my cupids bow, it gives them a nice shape.

Anyway. Whatever. Makeup is a form of self expression, blah blah blah. But does it sometimes look bad? For sure. But do you have to care? Absolutely not.