I agree with the ferengi. There is much pleasure in taking off nd imaing how you will take off a womans clothing.
In TNG, that's just what peopel wore. The style or lack of or 80s style they used was, hurpmf, uniform
DS9 changed that. layers. Lots of civilians. Loo-ooking good.
here's a thought.
What if if the Doctor just wan't hip?
he was twenty years behind the times.
Unless he was being retro or backward on purpose, as he wasn't dressing Seven like a sex worker, he was dressing seven like a grandma to AVOID the gal being drooled over and preyed on?
I'd also address the points that she was a child and had no practice or talent for dresing herself, and a few episodes of her looking like she was playing dress up in mommies closet would have been as Hilarious as Ivanova teaching Delenn about haircare. Child or not she had a huge empty space in place of this basic human activity.