Pretty much everything I know about life, I learned from Clueless. It is, hands down, the best fashion film ever made. Breakfast at Tiffany’s? Strong eyeliner game, but as a romanticisation of eternal unfulfilment and dysfunctional relationships, not a great blueprint for life. Clueless, on the other hand – which is celebrating its 20th birthday with the happy news of a Broadway musical in the works – is a veritable bible for living, with wise lessons to impart on the subjects of friendship, boys, sex, kindness, not to mention the rules of accessorising and the power of a white shirt. Watch and learn.
1. Never underestimate the power of clothes
Key line: “Cher’s main thrill in life is a makeover. It gives her a sense of control in a world full of chaos.”
Alicia Silverstone’s Cher Horowitz takes responsibility for her own destiny in every possible way. For instance, when she gets her school report card, she sees those grades as “a jumping-off point to start negotiations”. She is a gum-snapping, knee-sock wearing embodiment of Nora Ephron’s advice “to be the heroine of your life, not its victim”. Cher power-dresses for teenage life, and it works. Her very first look – a yellow tartan skirt suit, with coordinating knitwear and accessories – ensures she has the attention of the entire school population from the moment she walks on campus. She is evangelical about makeovers, which she insists on giving to everyone from frumpy teachers to grungy new girls.
2. Fashion should be fun
Key line: “I must give her snaps for her courageous fashion efforts.”
When Cher picks up her best friend, Dionne, for school, she makes a joke about Dionne’s hat looking like something out of Dr Seuss. Dionne makes a joke right back about Cher’s faux-fur backpack looking like a shaved dog. It’s all in good humour: they know they look kind of ridiculous, but they’re totally owning it. And look how it paid off: their Clueless outfits are so iconic that 20 years later, Iggy Azalea’s video for Fancy is a play-by-play remake of the film.
3. However glamorous you are, sometimes it pays to play the game
Key line: “Where is my white collarless shirt by Fred Segal? It’s my most capable-looking outfit!”
Cher has a tantrum when her Fred Segal shirt is at the dry-cleaner’s on the day of her driving test, which seems a little princessy – but you know what? She fails, so clearly she was right about the shirt. (Caveat to the Clueless-is-my-bible point: everyone in this film is a terrible driver. Do not take driving tips from this film. Personally, I blame repeat-watching of Clueless for the fact that it took me five attempts to pass my driving test.) Likewise, although twirling and tossing her blond hair is so much a part of her personal brand that Cher incorporates this into a high five, when she needs to win over a teacher or her scary dad she switches to a goody-goody Alice band.
4. Represent your generation, however dumb the trends are
Key line: “What did you do at school today?” “I broke in my purple clogs!”
The Clueless look is a riot of mid-90s fashion cliches: clogs, spaghetti-strap vests over white T-shirts, knee-socks, emo check shirts, overstyled pencil cases with pom-poms on everything. Some of this looks, frankly, awful – those choker necklaces with little pebbly gems hanging off, what were we thinking? – but some of the trends still work. Tai’s plaits, for instance, are very Braid Bar; Cher’s penchant for a backpack (she has a tartan one, a silver one and a white one) is completely on-trend. And Dionne’s bandana in the tennis-lesson scene is the exact same one Cara Delevingne was wearing side-of-stage for Kanye at Glastonbury.
5. Don’t overthink date dressing
Key line: “Sometimes you need to show a little skin. This makes boys think of being naked, and then they think of sex.”
Cher has a cheerfully low opinion of male intelligence and behaviour – high-school boys, in particular, are “like these nervous creatures that jump and slobber all over you. As if!” – and when she wants to catch a boy’s attention, her techniques are straightforward. A skimpy vest, hair piled up off the neck. Note, however, that Cher’s seduction techniques – showing skin, attempting to “have something baking” when a date comes round – don’t work. In the end, how she really gets her guy is by hanging out on the sofa with him in a T-shirt, eating snacks and swapping sarcastic comments.
6. Keep your standards high
Key line: “You see how picky I am about my shoes, and they only go on my feet.”
Cher is explaining why she is still a virgin when she says this, but the analogy holds across fashion, friends and snacks. (She doesn’t drink coffee, because she wants to be “five foot ten, like Cindy Crawford” – although nothing dates the film more than the amount of day-glo bright OJ these kids drink, in their innocent pre-green juice world.) Like her alter-ego, Jane Austen’s Emma, Cher tries her best at everything she does – even when the results are pure comedy.
7. Friends are everything
Key line: “Did my hair get flat? Did I stumble into some bad lighting?”
Ask your friends’ advice, and listen to it. When they ask for yours, reassure them they are fabulous. And when everything is going wrong, nothing beats getting the girls together for “a calorie-fest and the new Christian Slater”. (Footnote, for any youngsters out there confused by the Christian Slater reference: a long time ago, before he became associated with box-office turkeys and rehab, Slater was the ultimate teen heart-throb. Go watch Heathers and True Romance.) Also, she’s totally right about flat hair and bad lighting, which we all know are the sworn enemies of fabulousness.
8. For eveningwear, ditch the berets and pom poms and go simple, strong and classy
Key line: “It’s Alaia!”
Cher’s partywear formula consists of one block-colour dress – a red Alaia, or a white Calvin Klein – with a great evening coat. (Maribou feathered over the Alaia; sheer over the Calvin Klein.) Her commitment to minimalism is such that when her dad calls mid-party, demanding if she knows what time it is, she explains that “my watch doesn’t really go with this outfit”. Cher can also claim a piece of networker’s socialising advice that rivals Anna Wintour’s diktat of being in-and-out of any party in 20 minutes: on arrival, instead of heading straight for the kitchen/bar, she notes that one must “always do a circuit before you commit to a location”.
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