I don't think there's anything terrible going on here. I love people-watching, including clothes-watching, with one of my two uni age girls and we love spotting stylish looking people, and commenting favourably on stuff, people of all ages. We don't comment negatively as that would spoil it, but, also I do see a range of styles and sometimes I just realise that a style doesn't come over how I'd want to come over, and I mentally note that and don't wear it.
I don't wear floral midi-dresses or indeed any patterned dresses almost ever, it's not a style that I think flatters me and I don't think it flatters that many people, but I know everyone will say they weren't intending to look nice anyway...I do love dresses, just not that particular style and the way it is worn.
I love all the young people's styles at the moment, denim shorts and lycra tops, but I'm not going to copy them, that's their look, it's their moment, it's not for middle-aged me.
Watching other people, how they dress, how that reads to me and others is surely part of social life, especially for those interested in Style and Beauty, sometimes our thoughts are negative, sometimes positive. I also notice people who have an inner glow which is rarely to do with their clothes, one of my friends has this at the moment, just looks so healthy and buoyant in middle-age, it's a vibe.
I like the dress @IHaveNeverLivedintheCastle has been wearing, it wouldn't suit me whatsoever (in size/colouring), but it's a statement dress (to me) and not surprising people have been commenting on it, it's unusual and striking.