Trying to come up with a list of the five best dressed Winona Ryder characters is more difficult than one would imagine; it poses such challenging questions as, “do I include Mermaids or Little Women? Beetle Juice or Edward Scissorhands?”
Ryder is arguably the quintessential cinematic indie girl of the late 80s and early 90s, and narrowing down the list proved to be almost impossible. In the end, I had to cut some of my favourites (sorry, House of Spirits), to bring you the cream of the crop.

Lydia Deetz in Beetle Juice (1988, Tim Burton)
Before there was The Nightmare before Christmas, before the Johnny Depp collaborations, and long before the existence of any Hot Topic merchandise, Tim Burton was known in the cult film crowd as the director of a little film called Beetle Juice (well, that and Frankenweenie). Ryder was a relatively unknown actress at the time, but managed to hold her own alongside heavy hitters like Alec Baldwin and Micheal Keaton. Her character, Lydia Deetz, was the typical teenage outcast who dyed her hair black, dressed in macabre clothes – and befriended the household ghosts. With a sense of humour as dark as her wardrobe, Lydia was not one to be swayed by things like the paranormal or conventional styling choices.

“I’ve read through that handbook for the recently deceased. It says: ‘live people ignore the strange and unusual. I, myself, am strange and unusual.”

Veronica Sawyer in Heathers (1988, Micheal Lehman)
Veronica Sawyer stands as the alternative to the squeaky-clean, wide eyed heroines of other 80s teen movies (I’m looking at you, Molly Ringwald.) She dated the bad boy. She took down the popular kids at school, and got away with it. She had a fondness for plaid, shoulder pads, pouffy hair and croquet. She was dressed to kill, literally, knowing pleated skirts would be best for taking down the football captain and making it to homeroom on time. Not since the days of Bonnie and Clyde have a couple of murderous lovers looked so good.

“I have no control over myself when I’m with J.D. Are we going to prom or to hell?”

Kim Boggs in Edward Scissorhands (1990, Tim Burton)
The fact that one of Ryder’s most wholesome roles took place in a movie that featured a deformed man with blades in place of hands says a lot about the types of movies she stars in. Here, in her second collaboration with Tim Burton, she briefly returns to her natural hair colour to portray the popular but misunderstood Kim Boggs, who eventually falls in love with the titular character. Edward Scissorhands takes place in a Dr. Seuss-like world: pastel houses, hedges shaped like animals, and candy-coloured clothes that give the movie a wholesome appearance – except, of course, for Edward’s mansion.

“He didn’t skewer me!”

Lelaina Price in Reality Bites (1994, Ben Stiller)
A movie made to document the plight of Generation X-ers, thrust out in the real world with nothing to do. Lelaina, an aspiring filmmaker, was the valedictorian of her university and can’t manage to find a job beyond fast food and working at the Gap. Still she and her roommates manage to look good in the process with early 90s staples, including floral print dresses, doc martins, and baggy cotton shirts.

“He’s so cheesy, I can’t watch him without crackers. “

Susanna Kaysen in Girl, Interrupted (1999, James Mangold)

Like Audrey Hepburn in Roman Holiday and Mia Farrow in Rosemary’s Baby, Ryder’s role in this film is often simultaneously mentioned with her close cropped haircut. The film, based on writer Susanna Kaysen’s memoirs of living in a mental institution, takes place during a time of revolution in the 1960s. When not in a hospital gown, Ryder’s wardrobe is similar to her hairstyle: simple and minimalistic. She had us in the first scene when she visited her therapist wearing a horizontal striped long sleeved tee and black slacks.

“You know, taking us for ice creams in a blizzard… makes you wonder who the real whack jobs are. “

(all images from Film Stills)