From wastepaper baskets as hats to dresses made of mirrors – eight designers, musicians and comedians choose the one look that changed their life

‘The only problem is my toenails’: Evan Dando, musician and frontman of the Lemonheads

I have a photo of me taken in 1998 or 1999. It’s nothing out of the ordinary but I look real clean. I like the cut of the jeans, the nice boots, the good T-shirt; that’s how I like to think of my clothes. The moment is memorable because one of my best friends, Epic Soundtracks [from the band Swell Maps], had just died. I was in a rough place – but I was coming out of it. Things got better: I kicked drugs and met my wife Elisabeth.

What we wore when we were in bands in the 90s [the grunge look], it wasn’t a style, it was just what we wore. I actually love clothes. Now I wear corduroy trousers, a flannel shirt, jeans and sneakers. I don’t think anyone gets too old to wear nice things. The only problem is my toenails. They’re long and black because I haven’t worn socks in a while. I really need to cut them.

Facebook Twitter Pinterest ‘I look real clean’ … Evan circa 1998.

‘I copied Joshua Von Grimm’s look with no shame’: Charles Jeffrey, designer

I’d never wanted so instantly to look like someone than when I saw the Horrors guitarist Joshua Von Grimm’s outfit in the Sheena Is A Parasite video – director Chris Cunningham’s finest – in 2006. Those insane skinny cigarette pants and shirt, the white Chelsea boots, the inconceivably massive hair. I immediately copied almost everything about it with no shame.

It is one of my most formative experiences as a designer. It struck a match for me, the way it pulled things from history, but created something super-modern. Even though it is in some ways carefully considered, there remains something so immediate about it. It speaks to everything I like about fashion as a means of self-expression. It’s lofty and it’s kind of contrived, but it’s really alive. I love that.

Facebook Twitter Pinterest ‘It’s really alive’ … Jeffrey in 2006.

‘I wanted the audience to see themselves reflected in me’: Paloma Faith, singer/songwriter

Faith in the mirror dress.

At the start of my career I was interested in the idea that what I wore would become part of my performance. This dress sprang from that. I approached the designer Petra Storrs in 2008 with the idea that I wanted the audience to see themselves reflected in me, just as the songs I was writing about my personal life reflected their lives. It feels like a really important outfit because at the time I was performing in small clubs by night and auditioning for acting roles by day. It became a dress people remembered me by, “the girl in the mirror dress”.

I enjoy clothes that make statements rather than just look nice. I’ve kept everything of any significance I have ever worn. The mirror dress is now stored safely in two pieces in my loft. I am hoping my kid – or kids if I have more – will have fun with it in the future.

‘My hat returned to its former glory as a wastepaper basket’: Lucinda Chambers, stylist and former Vogue creative director

Facebook Twitter Pinterest In pursuit of her style DNA … an 18-year-old Chambers.

I was 18 and had just started at Vogue when I picked up a wastepaper basket and tied a huge taffeta bow round it to wear to a fashion show. It was the early 80s and before I even started working as a stylist. I was swept away by the avant garde aesthetic of Yohji Yamamoto and Comme des Garçons; this was a homage. My mother used to say, “Try things out”, so I made most of my clothes from materials I found lying around at home. This particular creation was incredibly uncomfortable but when I went to the cloakroom to take it off, it had left imprints around my forehead, so I couldn’t.

I think back to how oddly brave I was. But passion overrode the self-consciousness I might otherwise have felt. I was trying to find my look, experimenting in pursuit of my style DNA. As for my hat, it returned to its former glory as a wastepaper basket.

‘I chose words carefully to use as weapons’: Bella Freud, fashion designer

Facebook Twitter Pinterest Freud in her ‘Ginsberg is God’ jumper Photograph: David M Benett/Getty Images

I have always been obsessed by the power of words. As a furious and disillusioned teenager, I chose them carefully to use as weapons against my adversaries. One or two can convey so much.

I designed my Ginsberg is God jumper in 2002. I was making a short film with John Malkovich, called Hideous Man, about beatnik girls waiting at a club for their favourite poet to arrive for a reading. I wanted the leader of the group to wear a jumper showing her devotion to literature and art, like a band T-shirt. “Ginsberg is God” is funny, because what does it mean? Who is Ginsberg? It can mean everything and nothing.

Everything changed when Kate Moss wore it – it became a thing. It’s part of my identity now. I have lots from over the years and I feel like a worker when I’m wearing my Ginsberg.

‘It was a bold move at the time’: Paul Smith, fashion designer

A pivotal outfit for me would be two suits I had made while I was still living in Nottingham. I had three and a half metres of pale mint green and dusty pink gabardine, and had a suit made from each. The unusual colours were unique and an early indicator of my interest in tailoring. I wore the double-breasted green one with very soft, green handmade leather boots from the Chelsea Cobbler and the single-breasted pink one with burgundy patent leather boots from Camden Market.

It was a bold move at that time. Nobody my age was buying bespoke suits – it was something your parents or grandparents did. Young people all over the world were expressing themselves in different ways, such as the 1968 Paris riots. For me, those suits represented something individual.

Facebook Twitter Pinterest Smith in his first shop. Photograph: Paul Smith

‘My look has been a significant part of what makes me who I am’: Zandra Rhodes, fashion designer

This photo was taken in 1985 by Robyn Beeche and I’m wearing a piece from my AW81 collection, Renaissance/Gold. My look – including colourful makeup by Yvonne Gold and bright hair – has been a significant part of what makes me who I am and people recognise me for that as much as my designs. The jacket was part of my pleated crinoline collection. It’s a look that’s become a signature of my brand – for AW18 and SS19, I designed pleated dresses and jumpsuits using swirls and structured shoulders that fan out beautifully.

Pieces from the original collection are still relevant. They will be featured in this year’s Met exhibition Camp: Notes on Fashion. And I was asked to recreate the pleated tops I originally designed in 1973, worn by Freddie Mercury and Brian May, for the film Bohemian Rhapsody.

Facebook Twitter Pinterest Rhodes looking colourful in 1985. Photograph: Robyn Beeche

‘Wearing this outfit is when I became comfortable in my skin’: Gina Yashere, comedian

I wore a blue blazer with African print sleeves to do my Live At The Apollo comedy show in 2016. It cemented a new look for me at a new time in my life. It was by Stuzo Clothing, a non-gender specific clothing brand run by an amazing gay couple. Wearing it was when I became totally comfortable saying, “I’m out, I’m proud and I’m comfortable in my skin.” I cut my hair short and natural, and I started wearing glasses, too. Now I’ve got about 80 pairs.

When I was younger I used to wear my hair long to try to fit into what femininity was supposed to look like – even though my comedy has never been like that. Back then I cared what people thought. With age and experience, I’ve got to the point where I don’t give a fuck – I’ll wear what I like, take it or leave it.