I love to be comfortable and always have - the type of clothing you mention tends to be very uncomfortable unless you can afford the top end / bespoke side of it.
I was thinking the other day that it's interesting how wearing comfy clothes is seen as "not making an effort"or slobby, and trying to understand why asa society this is a common feeling. Why at work on a normal day we wear business attire which is very "old fashioned" and way more gendered than on dress down day when most of the men and women are in jeans tshirts trainers...
The only conclusion I could come to is that when getting "done up" maybe it's related to the thing of trying to emulate the people who have the money to wear these clothes easily becasue they are made for them and so fit and are in non scratchy fabrics. So it's a sort of aspirational thing.
Be interested to hear other views of why comfy is seen as an eyesore and "smart" is usually not comfy.
For me, although I am a comfy person, I really enjoy seeing people who "make an effort" - well at least if it's got a twist and is done for joy. When I was young I used to go to the goth clubs in london sometimes and the outfits! On men and women just amazing. Ditto I get a real kick from seeing people in vintage gear. At work, when a man goes the extra mile and has a snappy suit and a just so tie and so on, I will always pay a compliment, and the women who take the idea of a work dress and push it just enough into bold / eccentric. Love seeing unusual hairstyles / chaps with exoticly styled facial hair.
All good and if I saw someone on the school run done up and looking so happy to be in their swishy 50s dress or whatever then I would feel happy too. Small things in life.
If they can't appreciate that not everyone enjoys getting done up in clothes like that then they aren't just doing it for them, they are gaining a sense of superiority as well and in that case they can fuck off quite frankly. Live and let live is the motto here IMO.