Who’s Your Back-To-School Style Icon?

Even if it’s been a few years (or decades) since you strolled through the halls of your high school, you can still take style cues from some of the coolest silver-screen students.

Veronica Sawyer, Heathers

In the 1988 black comedy Heathers, the queen bee of the most powerful clique in school (a trio of girls, all of whom are named Heather) displays her prowess by wearing red. But the real style icon of Heathers is rebel Veronica Sawyer (played by Winona Ryder) who dresses in black and blue and dares to date a brooding outsider rather than dumb jocks. Of course, that brooding outsider turns out to be a major-league psycho who starts knocking off the student population, leaving it to Veronica to clean up the mess and lead the school into a clique-free new era… but we’re getting ahead of ourselves here.

This black-and-blue frock would be right at home in Veronica’s closet:

Top things off with a boxy blue blazer (the movie was filmed in 1988, so shoulder pads might even be in order in this case), black tights, and a black oxford-style heel.

Ideal arm candy: a sarcastic bad boy with expressive eyebrows and a penchant for wearing black trench coats.

Andie Walsh, Pretty In Pink

Everyone remembers the pink sateen prom dress worn by Molly Ringwald’s character Andie Walsh in the 1986 John Hughes teen-movie classic Pretty In Pink. Andie also rocked some seriously quirky outfits leading up to that point, accessorizing her thrift-store-chic ensembles with her signature granny pearls.

Pretty In PInk style requires a serious degree of slouch – think pleated pants rolled at the cuffs and printed blouses. Andie also liked her hats: black bowlers, cloches, you name it.

Ideal arm candy: Even though Andie ended up with the rich boy who decided he’d rather slum it with her than hang with his snobby friends, a good percentage of the movie’s fans believe John Hughes got it all wrong and that she should have ended up with her equally quirky BFF Ducky. Team Andrew McCarthy or team Jon Cryer? A tough decision. Perhaps Andie should have “changed teams” and ended up with Annie Potts…

Cher Horowitz, Clueless

You can’t talk about high-school-movie fashion without mentioning Clueless, director Amy Heckerling’s wonky take on the Jane Austen classic Emma. The air-headed-yet-warm-hearted Cher Horowitz (played by Alicia Silverstone) became a 1990s pop-culture touchstone, both for her charming L.A.-speak catchphrases (as if!?) and her over-the-top outfits, organized in a computerized closet.

For the most part, Cher’s style is matchy-matchy and adorably twee:

Pair with an argyle-patterned cashmere cardigan, knee-high socks and chunk-heeled shoes and make sure your hair is extra shiny.

Ideal arm candy: skip past all of Cher’s mistakes in chasing the boy who looks good but would rather, ahem, “watch Spartacus” than canoodle, and go right for the intellectual confidante who sees the real person behind the style (if he happens to look like Paul Rudd, all the better).

Get our Shopping & Style newsletter for local fashion, decor and retail inspiration emailed to you each week.

Related posts

How to Phone in the Holidays in Calgary

K├Ąthe Lemon

The Best of 2019: Our Favourite Rooms

Sam Gryba

Inside Larry and Adele Thomson’s Downtown Calgary Condo

Amber McLinden

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Privacy Policy

Privacy & Cookies Policy