black collared dress Button-Up button placket continues past a banded waist and down to a flaring skirt with front diagonal pockets Collared Button Down Mini Dress

Chase it all with a SkinnyGirl margarita and marathon of the most outstanding episodes, ranked from most dramatic to semi-dramatic

This black cardigan sweater dress by Open Edit can be worn as a longline cardigan OR as a dress

Preppy Meets Casual All did not subscribe to grunge or sporty appearances

The shoe style works just as well with minidresses as with a midi-dress, and tights wont throw off the look either

Her skirt is made from green tulle with a satiny harlequin overlay (just used one of my skirt tutorials for the skirt

These looks remain part of the pop culture conversation decades later, reappearing in everything from editorial shoots to TikTok trends