I wouldn't wear the New Look ones with a skirt, no chance!
I do like a chelsea boot myself but I infinitely prefer them with a sharp pointed toe, which (luckily for me) is coming back into fashion again. I have trouble finding the ones I really like in my size, always have done since I was a teen (Euro 41 -42, most only go up to a 40) but sometimes I get lucky.
The ones I bought recently were fairly pointy though - I can't stand the rounded toe (mum boot) look as I have such big feet - the point offsets the size - and square toes would be even worse!
You don't have that issue because you have small feet. But I still wouldn't wear those chunky ones with a skirt.