It seems that the community is pretty well aware of the series Paradise Kiss by Ai Yazawa, which features plenty of fashionable characters. But have you heard of its prequel?
Gokinjo Monogatari (Neighborhood Story) came out in 1995. It follows the lives of a group of fashion students. A number of styles are represented, but I wanted to share some screencaps of one particular character, P-chan, who donned some adorable 90s Lolita outfits!
In the show, she is portrayed as loving dolls and childish things, constantly carrying around her teddy bear named Pucci Francois. She's a sweet, loveable girl and kind friend to the others. Her outfits often feature some kind of hat and frequently involves plaid in various colors. I like how cutesy-carefree she is and how poofy her pigtails are under her large-brimmed hats and headbows <3