Quick: How do you tell if a woman in a movie is supposed to be intelligent? First off, she’d probably be brunette, but past that. Glasses, yes. Little to no makeup. Her hair is probably in a ponytail. Clothes she probably bought at the Gap in a size too big. You know she’s the smart one because she thinks about more important things than her appearance.

It’s a stereotype, yes, but it’s constantly reinforced by intelligent women who should know better. Germaine Greer rallied women to taste their own menstrual blood in The Female Eunuch and then attacked fellow feminist writer Suzanne Moore by stating that “so much lipstick must rot the brain.” Feminists must reject the male gaze and use those ten seconds it takes to apply lip gloss to bring down the patriarchy. (Why sensible feminists have not figured out how to band together and write press releases to disassociate ourselves from the crazy women who pretend to speak for us, I’ll never understand.) Fashion magazines don’t help much either. Elle talks to Ashlee Simpson. And writes down what she says. To be recorded for all time.

If you’ve ever read one of the hundreds of books on the market telling women how to dress and how to shop, you know why fashion writing needs some more smart girls to come over to their side. These books exist, and are in some ways needed, because there is a huge disconnect between the fantasy world of Vogue — where women spend their days romping in fields wearing $1,500 sequined leggings — and reality. Yes, those egg-shaped coats look charming in the magazine, but can someone who weighs more than 80 pounds wear one? The magazines won’t tell you because to them, no such woman has ever existed. Not every woman can afford to hire someone to make these decisions for them so some may need help deciding what works on their bodies.

Instead of alleviating our body fears, however, so many books advising what to wear do nothing but exaggerate them. The entire structure of Trinny Woodall and Susannah Constantine’s book What Not to Wear is built to help you define your particular version of body dysmorphic disorder. Do you think you have short legs? A big butt? Big arms? There’s a chapter telling you how to dress around each perceived flaw. It’s hard to walk out the door feeling hot and feisty when your entire dressing process has been focused on your main source of anxiety. If I tried to dress to hide all the parts of my body I have ever been self-conscious about, the only thing left to wear would be a hazmat suit.

Then there are the “shopping guides.” A book telling you how to shop seems ridiculous until you accidentally wander into H&M on the day a limited edition line is released. You suddenly have to decide in 10 seconds if the ruffled collar on the Viktor & Wolf dress is really you, because there’s a 14-year-old girl tugging on the other end of it. At some point you’ll probably spend hundreds on a coat only to find the price slashed 80 percent the next week. A strategy might come in handy.

It’s strange that the shopping guides still exist in book form now that there is Lucky magazine, but they continue to come out every season, identical to each other and utterly disposable. Susan Redstone has written one of the latest shopping guides, Just Try It On! A Month by Month Guide to Shopping and Style. It sounds so approachable, like Redstone’s a friend holding your bag outside the changing room. But she’s more like the sales clerk who’s thinking only of her commission when she says you look elegant in a skirt you are obviously 10 years too old for.

Redstone wants you to pull out that credit card to buy absurd things, like a “stable” of designer bags. Nothing being sold on the sidewalk, because “many of these are illegal and usually trace back to dodgy production in rural places where labor laws and copyright laws are broken with abandon.” Before you start thinking she’s just worried about ethics, you should note she has no problem with sweatshop sneakers or even fur. It’s the word “rural” that sticks out, as if she’s most offended by the idea that the bag was sewn in a place where cows are milked.

Never has shopping sounded like less fun than it does with Redstone. She advises women to create a persona to guide all their shopping choices. “Before trying something on or making a purchase, you should ask yourself, would my alter ego, the aristocratic heiress, buy this pocketbook?” Redstone does not simplify shopping, she complicates it. I first have to create a persona based on my favorite drink — she gives examples for dirty martinis and champagne, of course, but strangely there’s no advice for us straight whiskey drinkers. I should try to schedule my shopping around my menstrual cycle to avoid feelings of low self-esteem. Redstone just parrots back all the marketing nonsense that is forced upon women, and nowhere is that more obvious than in her endorsement of the “right hand ring.” Developed as a way to boost diamond sales after those pesky stories about the jewels’ funding civil wars and killing children came out, they’re marketed towards single, professional women. Why wait for a man to buy you a diamond ring? Buy your own and flaunt it like a “Single and Lovin’ It!” bumper sticker. Redstone calls the idea “liberating” and “ingenious.” I call it “disgusting.”

It makes me wonder where Hadley Freeman has been all my life. (Writing for the Guardian, apparently.) Her new book The Meaning of Sunglasses: And a Guide to Almost All Things Fashionable will not make you feel worse about the state of your thighs, nor your brain. Freeman namedrops Andrea Dworkin and poet Joseph Parisi as often as she does Anna Wintour. She’s the one you want on the other side of the changing room, not Redstone. If you came out looking cheap, she would grab you by the shoulders, turn you around, and demand you change immediately. As she writes in the section labeled “Cleavage, and the plumbing of depths,” “Show me a woman with a good three inches of cleavage on display, and I’ll show you a woman who, rightly or wrongly, has little faith in her powers of conversation.”

Freeman wrote a book for women who actually exist. Women who have to wait for buses in the middle of winter. Women who like to dance at parties, and do not want to have to sit in the corner because their feet are bleeding. She knows that these women live in the real world, where fur is not harvested from free-range chinchillas that all die of natural causes (see “Fur: bad”).

She also knows that clothing is not about a set of rules or dressing to please men. “Fashion should be about self-expression, and if your self has a little more going for it than worrying about what pleases either of the two pillars of fashion dictatorship – men’s mags (tight, short, available) or TV-style makeover shows (fluted sleeves, bias cuts, unthreatening) – then flaunt it to the world, and if they don’t like it, that’s just too bad.”

If more fashion writing was done in the tone of smartypants Freeman, we could avoid the fear that caring about our appearance makes us a vain fool or a victim. A work colleague recently took one look at the four-inch peep toe heels I was wearing and snarled, “Don’t you know why men invented high heels?” I doubted anything I said would deflect what was coming next, so I just shrugged. “So you can’t run away when they want to rape you.” I understand. I used to be a humorless feminist, too, complete with shaved head and my father’s combat boots. Then I discovered Charles David heels and got over it. If only The Meaning of Sunglasses had existed sooner, I could have spent less time being a self-righteous twit. • 20 February 2008