Most Iconic Chick Flick Outfits | Get the Look

What’s better than a night in with your besties watching your favourite chick flick? Endlessly rewatchable, the stories are woven with hilarious one-liners, crazy characters and killer outfits. Not only did these films teach us a little bit about love and friendship, they taught us a lot about fashion. Our favourite chick flick outfits were unforgettable – think of Cher Horowitz in that yellow two-piece, Regina George’s velour juicy tracksuit, or Elle Woods in the hot pink leather number. Three fashion icons that had us obsessively googling ’90s and noughties style.

#1 What did they wear in the 90s?

An era defined by warring sub-cultures, the ‘90s can’t be reduced to a single aesthetic. If you want to remember the preppy side like Cher, think of slip dresses, scrunchies, mini skirts and mules. To remember the Nirvana fuelled rise of Grunge, think oversized plaid shirts and ripped jeans with Dr Martens. If you want to go back to a time when Tupac was still alive, try some baggy jeans, a cropped white vest and pristine sneakers.

#2 How do you dress like the 2000s?

A world where Paris Hilton reigned supreme and Kim Kardashian was just cleaning her wardrobe, the noughties are known as the time of tackiness. Although Punk, Scene, Emo and Streetwear styles were on the fringes, oversized sunglasses and juicy tracksuits are the things we like to remember. Think OTT girly girl and imagine Paris in a skimpy skirt, wearing stilettos with a halter neck top, holding her diamante encrusted Motorola.

#3 Fashion lessons from our favourite chick flick outfits:

Our three favourite films for ’90s and noughties fashion have to be Clueless, Mean Girls and Legally Blonde. Each of our three blonde bombshells go on a journey of self-discovery, while always being the best dressed. Here are some of our favourite chick flick outfits and the styling lessons they taught us.



As if we could do the most iconic chick flick outfits without including the fabulous Cher Horowitz. The queen of plaid, Cher is loved for her impeccable taste, buggin’ burns and loving nature. Although she assures us that she’s ‘totally a normal girl’, her computer closet was way ahead of its time.

Named as Alexander Wang’s favourite film, Clueless heavily influenced the ‘90s and still inspires fashion today. Rebelling against the grunge aesthetic of the time, Cher’s preened style started the wave of preppy minimalism. Flawlessly pairing slip dresses with scrunchies and trimming everything with fur, the wardrobe in this film is to die for. Cher’s iconic yellow two-piece still turns up every Halloween and was even worn by Iggy Azalea in her chick flick inspired music video.

If you like preppy, pristine and plaid looks – Cher will be your go-to style guru. Here are some styling lessons we learnt from Cher Horowitz.

#1 Plaid is like totally the best print


Clueless made plaid mini skirts a major piece of 1990s pop culture. According to Cher, the skirt can be A-line or pleated, as long as it’s mini. Depending on what colour you choose, the skirt can go from punky (think black or pink) to preppy (something bright, like red or yellow). Pair it with a matching tailored jacket to make a statement.

#2 Layering is everything


Cher shows us that layering can take any staple item from a five to a straight ten. Go for any fabric you like, as long as the necklines differ. You’ll need to pair something high, like a turtleneck, button-up collar or crewneck, with something low, like a strappy crop top. If the hemlines differ too – even better. Although the grandpa vest and white shirt combo has come back with a vengeance this season, Cher Horowitz was doing it 25 years ago.

#3 Sheer shirts are a must


Another great piece for layering, sheer shirts are a wardrobe must-have. Undeniably sexy while still remaining chic, sheer takes a classic shirt from day to night wear. Pair it with a tonal strappy top for a smouldering style.

Mean Girls


Probably the most quotable chick flick of all time, Mean Girls taught us that anything mini is so fetch and trying to be anything but yourself is truly plastic. Released in 2004, this film captures the best bits of noughties fashion with some of the hottest chick flick outfits ever. Taking us back to a time when girls wore stilettos to school (thank god that impractical trend has been left behind), the fashion in this film is girly gone wild.

So, get in loser, we’re going shopping.

#1 Mini purses are a girl’s best friend


Mini skirts, mini purses, mini dresses – the fashion in this film always opts for fun-sized. Not only do they fit comfortably under your arm, mini purses level up any look.

So you agree? You think mini bags are really pretty? If you want to capture this noughties style, pair it with a slogan tee and colourful cardigan. If you want a more modern look, wear it with an oversized T-shirt and straight leg jeans.

#2 More is more


Why have a medium when you could have a large? That seems to be the motto of the Mean Girls, pairing crop tops with mini skirts and stiletto heels. Pink is a colour not just for Wednesdays, but a staple in any Plastic’s wardrobe. Being cool in the 00s was not looking like you’d made the least effort, it was going for gold with larger than life outfits and regular lip gloss upkeep. If you want to nail the noughties trend, replace ‘less is more’ with as many diamantes as you can find, channelling your inner Paris Hilton.

#3 Loungewear doesn’t have to be slobby


Who said loungewear can’t be stylish? Velour tracksuits are synonymous with noughties fashion, and this film is Juicy obsessed. Go all out with a matching set for lounging at home or pretending you’ve been to the gym. Juicy tracksuits are definitely back in, but if you want more modern loungewear, check out Olivia Rubin.

Legally Blonde


Despite coming out nearly 20 years ago, Legally Blonde top the charts with some of the best chick flick outfits of all time. Known for her bleach blonde hair, bright pink wardrobe and matching companion Bruiser, Elle Woods is a fashion icon. She taught us that you don’t have to give up glamour to be taken seriously, and most importantly, how to bend and snap.

If you’re after something bold, ultra-feminine and super-cute, Elle is your girl. Here are some of the styling lessons we learnt from the one and only Elle Woods.

#1 Go big or go home


Casual is not a word in Elle’s vocabulary. Pink, fluffy, sparkly or furry – anything Elle wears has to fall into one of these categories (sometimes, all four). Elle’s uplifting outfits make her stand out against the crowd and she is never afraid of being “too much”. Next time you look in your wardrobe, try to channel some Elle Woods energy and pick out that item you’ve been too shy to wear.

#2 Don’t shy away from bold colours


If you’ve gotten stuck in a boring rotation of black, white or grey – take a leaf out of Elle’s book. Bold colours are a great way to brighten your day, and despite Elle’s personal preference, it doesn’t always have to be pink. If you’re new to this, pick out a simple silhouette in a bold colour to get you started.

#3 Workwear doesn’t have to be boring


Just because work can be boring, doesn’t mean your clothes have to be. In this courtroom look, Elle nails conservatism without losing her signature style. Still pink, still flattering and still sparkly, this outfit is both fashionable and appropriate. A simple collar or lapel can take any dress from summer casual to workwear chic.

Find the perfect accessory to go with any of these looks, here on MyBag.

Looking for more film fashion? Check out our favourite looks on Monica Geller for something more casual. Or, discover our style lessons from Julia Roberts’ Notting Hill outfits for something more chic.

Written by Gigi Gordon

Sarah Atkinson

Sarah Atkinson

Writer and expert