Instead​ of the new season fantasy every woman is instructed to have as autumn approaches, this September I dreamed of throwing all my clothes out. Things that I used to turn to – a purple boiled wool cocoon dress, a swishy black midi skirt, a sheer silk blouse with a print of parrots and parasols – disappointed me. My clothes, I noticed, were mostly the colours of a bruise as it appears and disappears: black to purple to blue to clotted burgundy to brown to mustard yellow. I had several collections of near-identical garments: two yellow skirts, four black skirts, three stripy tops, three pairs of scuffed black ballet flats, and a grey cardigan I wanted to lose. Did I think I was building a style or was I just refusing one? Everything I put on reflected something bad about me.

There are several collections of clothes in Sheila Heti, Heidi Julavits and Leanne Shapton’s book about the problem of dressing, Women in Clothes (Particular Books, £24): from the impossibly glamorous 16 fur coats in teddy-bear shades belonging to Marlene Barber to the mundane 47 hair grips, black and bowed, belonging to Amy Pinkham. My proliferating black skirts seemed a sign of lack of imagination, but perhaps obsessively collecting one article of clothing needn’t in itself be bad. Could it be a refusal to surrender to good taste and the tyranny of the capsule wardrobe? Collections say: I like aviator sunglasses, vintage dress sets, nail polish, brassières, wrap skirts or boyfriend shirts, and I’m going to wear them.

Heti had looked for a book that addressed ‘personal style as a way we speak to the world’ and been dismayed by the Audrey Hepburn picture books she found, so she asked Julavits and Shapton to help her assemble one. They put out a questionnaire – Do you notice women on the street? If so, what sort of women do you tend to notice? What are some dressing rules that you wouldn’t necessarily recommend to others but that you follow? When do you feel at your most attractive? In what way is this stuff important, if at all? – and the book that comes out of the answers, from some you’ve heard of but most you haven’t, has all the pleasures of eavesdropping. The editors are also the best collectors in the book. Here are the situations in which women feel at their most attractive: before leaving the house, after sleep, after sex, after being good, after swimming in the sea, after going to the hairdresser, when pregnant, when ovulating, while running, when thin, on a sunny day, when naked and wearing heels, when flirting, when painting, when dancing, when dirty, when drunk, when alone, when invisible.

Dressing is difficult because, as Leopoldine Core answers, ‘we are always asking for something when we get dressed,’ and so we have to have some idea of what we want. Five-year-old Milena Rosa agrees: ‘Sometimes I know what I like, and sometimes I don’t really know, ’cause I forgot right then what I like.’ Lena Dunham needs to inhabit a part; Roxane Gay looks at the clothes in her wardrobe, thinks she might wear something different for three minutes, then picks one of the ten outfits she wears all the time; Eufemia Fantetti wore trackpants for a year before her father asked whether she wanted to look nice: ‘Who am I supposed to look nice for? Every man on the street?’ ‘Why not?’ her dad said. ‘What’s wrong with that?’ A dress’s best destiny may be to hear it’s the most interesting at a party, but there is also the whoosh of casting a spell over yourself: the woman who bought a wedding gown when single and put it in a chest ‘had found something that would be perfect for an occasion that might happen, and it did’; the saris that make a kssshh sound as two women pass in a doorway, the pink ribbon belt next to a naked waist, the socks that read ‘I don’t give a fuck.’ And the mysteries: why do bikinis make you look so much worse than you do naked? ‘Who is the woman,’ the worker in Vietnam double-stitching underwires into bras asks herself, ‘who will wear the bra I am sewing?’ And the power: Sadie Stein admits that offering an ex’s new girlfriend something from her own wardrobe gives ‘a rush of euphoria and relief’; Gayle Davies is banned from sitting next to her sister in church because she’s in pink and her sister is in red. But dressing well also involves the possibility of being misunderstood, the problem of living in doubt. ‘People with style,’ the art historian Alexander Nagel tells Heti, ‘maintain a sense of starting over, a sense of knowing how to do it, but also learning how to do it at all times.’

My idea, once all my clothes were gone, was that I would choose one outfit and wear it until I found something I liked better. And I discover that the sculptor Michele Oka Doner has mostly worn one dress for 27 years. She has had it made forty times, in different fabrics: white for the Miami summer and black for the New York winter and grey for inbetween times. It is softly toga-like; you pull it over your head. She specially likes the way it frames her face. (The man who designed it lives in a trailer in upstate New York and is in a dispute with a neighbour over a cat.) It ‘allows me such great freedom … the dress is transcendent.’ Could dressing be about transcendence? Ida Hattemer-Higgins bought a green Yves Saint Laurent pencil skirt, a linen dress with a double Peter Pan collar, shirts in salmon, indigo and turmeric silk, a dove-grey swing jacket and a camel-mustard coat on a trip to Athens with the fiancé she’d recently broken up with. ‘New clothes are the solid tip of the future,’ she writes. She would give away the wedding dress she’d bought with care and go to Paris with just these clothes: ‘I seem, to paraphrase Chekhov, to be asking more from fashion than it can give, because the source of my fascination is a dream.’ When I throw away all my clothes, I could always replace them in Paris.

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