Clothes on Film is a series in which we explore iconic looks from film and television that have stayed in our minds years after they first hit the silver screen.
Chronologically sandwiched between The Breakfast Club  and Clueless , Welcome Home Roxy Carmichael  isn’t always the first film that people think of when they picture an epic makeover scene. But Dinky Bossetti [Winona Ryder] experiences a transformation worthy of attention.
Dinky is a girl who “prefers books to dolls and boots to ballet slippers,” as her character eloquently puts it in the film. Even if you couldn’t relate to her dark and apropos ‘90s wardrobe—more on that in a minute—you could relate to how she felt like an outsider. So when she arrives at a party anticipating the homecoming of Roxy Carmichael, who Dinky suspects may be her birth mother, she opts for a floaty pink gown worthy of the prom queen title.
We asked costume designer Betsy Heimann to tell us about the wardrobe she created for Dinky (since Ryder herself was the original queen of goth) and how the scene with the pink dress at the homecoming celebration transformed not just her wardrobe, but also her character.
HEIMANN: I remember that I made Winona that dress—it was one of my very early made-to-order custom designs. The interesting thing about it was that it was a real breakaway moment for her character, because she was early grunge. Grunge wasn’t all that happening at that time. I washed all of her clothes in dirty black water—everything she wore in that movie was over-dyed black. It’s as if you took your black jeans and in those days the dye wasn’t good and if you washed anything with your black jeans [laughs] it came out grey. So I kind of did that, literally. So for her to have this frothy moment…I wanted that netting and then that ruching all around Winona…so tiny, so delicate. Just to enhance her vulnerability and especially that choice of color because she was really going outside of her comfort zone. And I thought that if she was going to really take a risk in that moment that it would be good to use a risky color—to give her something that was fitted and frothy all at the same time. And I know Winona really liked that dress.