Written by Bertie Bowen


Dressing Like… Cher Horowitz

Fashion stylist Bertie Bowen channels the clothes and spirit of a fictional character. This week she’s looking at a 1990s teenage heroine who’s seriously like, whatever. Why wouldn’t you want to dress the same? Like, duh.

Clueless posterWhen the idea for this column was initially suggested to me, Clueless was one of the first films that popped into my head. It was also the most popular suggestion from my friends. When this film was released in 1995, it blew my tiny, teenage brain. I watched it again last week while downing a bottle of red from an inappropriate vessel (I’d moved house that day) and my brain was blown all over again.

Based roughly on Jane Austen’s novel, Emma, Clueless was written and directed by a woman, Amy Heckerling, which could be why it speaks to my generation of females so powerfully. Heckerling created a female lead who is beautiful and naive, but also witty, caring and fiercely self-assured. And her style perfectly captures a particular age, attitude and era. Let’s relive our awkward teenage years.


In the opening scene of Clueless we meet Cher Horowitz, a wealthy valley girl getting ready for school and choosing her outfit with help from a computer program. WOW, it seemed so futuristic. Except this computer only seems to know how to create perfectly matched ensembles: your skirt must match your jacket which must coordinate with your shoes which should also complement your bag, which must tie in with your hat and synchronise with your socks. Colours, prints, fabric – everything must go with everything else. Someone must have made an app for this by now, surely?

PLAID: is popular

As mentioned above, matching your skirt to your hat (et al) is vital for the Cher look, so why not also try out one of her favourite patterns: plaid. To say plaid is popular in Clueless is a massive understatement; there are 53 types of plaid worn in the film, seven of those by Cher (ta, IMDB!). Cher wears her plaid head to toe, in garish colours such as sunshine yellow or baby pink.


Skirts and shirts are typically smart, office attire. Not in Cher’s world. Think Laurence Llewellyn-Bowen with your shirts: oversized cuffs and large pointy collars – the bigger the better. Cher usually wears a skirt and it is always, without fail, arse-skimmingly short. Who can blame her? She has great “stems”.

SOCKS: high and surprisingly deep

Cher wears her socks knee high, or my favourite (for probably far too long into my 20s) – over the knee. Strangely sexy but also inappropriately childish, socks are a perfect metaphor for Cher’s character: at the cusp of womanhood yet still utterly clueless.

Alicia Silverstone in CluelessLAYERING: epitomises the 1990s

Until I watched this film again recently I had completely forgotten the ‘90s art of layering. Cher likes to wear either a tank top over the aforementioned shirt or a cropped vest over a white t-shirt. If this look hasn’t been reproduced on the ASOS website recently I’ll eat my hat, which brings me to my next point…

TOP IT ALL OFF: accessorise like there’s no tomorrow

Cher loves accessories. She sometimes wears a beret or a wide hair band and for updos (and I mean an on top-of-your-head bun or high-as-you-can ponytail) you’ll need to invest in a scrunchie. To carry your massive cell phone, an impractically mini backpack, preferably in a shiny, cheap-looking material is ideal. Shoe-wise, Cher is fond of a Mary-Jane, platform or purple clog.

Cher’s style may be incredibly girly, mirroring her youthful (at times self-absorbed and daft) attitude. Yet don’t be fooled by her saccharine appearance. Cher is a tough cookie. She is full of snappy comebacks and droll one-liners. She plays up to her pretty bimbo looks but can stand up for herself when it matters. She doesn’t take any shit. And dressed like Cher, neither should you. Girl power.


Has Clueless stood the test of time? Rebecca Humphries rates or dates it.

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Written by Bertie Bowen

Stylist, writer and mother living in East London. A clompy shoed, curly haired, Radio 4 enthusiast. www.mothershoppers.com