Finding 'first day' fall inspo from teen queens past

Your iCal may say that the new year begins on January 1st but the beginning of a fresh school session still feels like hitting the reset button for many of us, even long past our school year. Now is the time to set out who you'll be this year, sartorially speaking. So why turn to characters from cult classic movies like Cher from Clueless, Enid from Ghost World and Nancy from The Craft for inspiration for that 'first day back'? Because these unlikely heroines left an indelible mark on the teenage experience portrayed on the silver screen.

High school is often pegged as a time for fitting in and finding your tribe. In stark contrast, these women were unabashedly themselves, no apologizing for their personalities or style preferences. IMO, that makes them trailblazers in the face of the typical teen narrative the one that insinuates a cookie-cutter makeover will land you the cute quarterback and guarantee the prom queen tiara. Now more than ever, their self-confident message rings true.

We are finally in a time that celebrates individuality. Magazine covers are showcasing greater diversity, ads are targeting larger audiences and brands have been quick to jump on the bandwagon too - there are dozens of lines whose popularity hinges on personalization. Clearly ahead of their time, these iconic characters are deserving of their teen queen titles, and it's time we take a page out of their style book.

Cher's yellow plaid suit, Enid's graphic tees and Nancy's gothic blacks have stood the test of time. So I've rounded up the pieces that will help you channel your fave high schooler this September. And if you remember nothing else, take Shakespeare's sage advice to heart, and to thine own self be true.

The posh prepster

Initially reserved for wealthy ivy leaguers, preppy style emerged in the early 20th century on campuses across eastern America. It was designed to cater to leisure pursuits (like polo, golf, rowing and tennis), which explains why pieces like oxford shirts, cable knits and boat shoes were so popular. By the '50s, it had spread to the masses who wanted to look like they lived that lifestyle too (who wouldn't?) and hasn't showed signs of waning since. If you idolize the style of Jackie Kennedy, Kate Middleton and Blair Waldorf, this is the look for you. While Cher Horowitz's '90s closet (filled with mini bags, Mary Janes and spaghetti straps) is a far cry from the trappings of traditional preppy style, her sweet cardigan, punchy yellow plaid and white knee highs all nod to the original buttoned-up aesthetic. It's a simple, easy approach to dressing, especially if you go the suit route. But maybe swap the single strand of pearls for a feathered pink pen - Cher wouldn't be caught dead in class without it.

Guess + UO Plaid Trucker Jacket, $98, urbanoutfitters.com

J.Crew Cotton Jackie Cardigan Sweater, $59.50, jcrew.com

Moschino Phone Case, $15.99, amazon.com

Janessa Leone Isobel Hat, $104.66, shopbop.com

The chic geek

Fashion has embraced the geek. Need solid evidence? Look no further than the runways where big glasses got the Gucci treatment and Stranger Things tees appeared at Louis Vuitton. These days, it's cool to be the class nerd. Whether you're all about wearing your fangirl faves on your sleeve or simply wanting to stand out, this is the look for girls who dress to the beat of their own drum. Oddball combinations, like Enid's graphic tees, Dr. Martens boots and bucket hats are fair game. Since there are no rules, don't be afraid of clashing colours and interesting textures, it's all about showcasing your individuality in pieces you love.

Coach Embroidered Rexy T-Shirt, $175, coach.com

Topshop Check Kilt Mini Skirt, $54, topshop.com

Dr. Martens Iced Metallic 1460 Pascal, $159.99, drmartens.com

Isaac Mizrahi Glasses, $80, clearly.ca

The goth girl

Think you're a true original for drawing on thick black eyeliner and wearing lots of leather? Sorry to burst your bubble, but the goth look has been around since the '80s. It grew out of the punk music scene in England and still has ties to those moody melodies. But, you don't have to have been a punk rock or wiccan (like Fairuza Balk who played Nancy in The Craft) to head back to school wearing safety pins. Just a little anti-establishment yourself! Sure you might have a rebellious streak, but more often than not, you use your style as a way to distinguish yourself from the pack, and if your look is not for everyone, that's ok. Just like The Craft's coven of teen witches, it's all about finding friends who like you for you (choker, leather jacket and witchy shoes included).

Zara Faux Leather Biker Jacket, $79.90, zara.com

See By Chloe Asymmetrical Hem Dress, $680.26, shopbop.com

Thomas Sabo Royalty Cross Choker, $271, thomassabo.com

Dior Rouge Dior Liquid Lipstick in Black Matte, $43, sephora.com

Caitlan Moneta (@caitlanmoneta) is a Toronto-based fashion editor, writer and stylist. She's a firm believer that there's nothing a little retail therapy can't fix.