When a record exec invited teenage Sinéad O’Connor to lunch, he told her to wear miniskirts and grow out her short hair. In response, she marched straight to the barbers to get a buzz cut. It subsequently became one of the most iconic buzz cuts in music. The late singer – who changed her name to Shuhada Sadaqat in 2018 after converting to Islam, but still performed under and answered to Sinéad – maintained the hairstyle, taking a razor to her head approximately every 10 days. The look complemented her skinhead punk-meets-90s normcore personal style: a uniform of leather jackets, slogan tees, straight leg denim and Doc Martens that cemented her place on many 90s revival mood boards.
Sinéad soon became as known for her striking look and outspoken views as she did for her music. Both expressed her defiant personality, one at odds with how women in music were ‘supposed’ to act. After all, she never planned on becoming a popstar. She simply wanted to be a protest singer. Her confrontational attitude got her into trouble, most famously during a 1992 SNL performance where she tore up a photo of Pope John Paul II live on air in protest against child abuse within the Catholic Church – what viewers didn’t know until later was that the photo itself had been the only picture on her abusive mother’s wall. The fallout was so controversial that when she performed at a Bob Dylan tribute concert at Madison Square Garden soon after, she was booed off the stage.
Sinéad represented true authenticity, never letting other people dictate how she should look or behave. To celebrate the Irish singer’s life following her death on 26 July 2023, we look back at her most iconic outfits from that era.
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At the Olympic Ballroom Dublin, 1988
From the very beginning, Sinéad’s style purposefully defied expectations. “I know loads of people who’ve played my records to people who’ve never seen me before,” she told NME in 1988, “and they always say, ‘She’s very small, she wears Laura Ashley dresses and she has dark black hair,’ because I’m Irish and that’s what they think Irish women look like.” Performing in her hometown of Dublin that year, Sinéad wore a cropped biker jacket and Doc Martens, hard punk staples only softened by her choice to style them with a tutu. It was punk, but with a feminine twist: a visual representation of the dual strength and vulnerability contained in her music.
At the Grammys, 1989
Two years before Winona rocked a similarly iconic leather and denim combo, Sinéad turned up to the Grammys in a heavily embellished biker jacket and white T-shirt featuring a pop art Virgin Mary, one of her earlier subversions of Catholic imagery. The lowkey look expressed her disdain for the awards show. Two years later, the then 24-year-old Sinéad became the first artist in the awards’ history to boycott the Grammys, lambasting the music industry for promoting false and materialistic values rather than artistic merit. In an open letter to the Academy, she expressed these views, in turn explaining the reasoning behind her understated wardrobe: “We are allowing ourselves to be portrayed as being in some way more important, more special than the very people we are supposed to be helping — by the way we dress, by the cars we travel in, by the ‘otherworldliness’ of our shows and by a lot of what we say in our music,” she wrote. The singer refused to accept any awards she won, despite being nominated for four, including Record of the Year, proving she was willing to put her career on the line to stand up for her beliefs.
Wear a condom T-shirt, late 80s
The first time Sinéad appeared on TV, it was in a mock-up advert for a fictional condom product, during a time when condom advertising was still banned on British TV. The fictitious commercial was part of a two-part special for the BBC called AIDS: The Last Chance which was broadcast in 1986. “The reason they asked me to do it was because I neither looked like a boy or a girl, they wanted somebody androgynous,” Sinéad said. She continued to support the cause of raising awareness about the AIDS crisis and contributed to a fundraising album in 1990. She also publicly criticised the Church and the State for not legalising condoms in Ireland until the 1980s. In the 80s, Sinéad humorously posed pregnant for a photo promoting condom use taken by British photographer Kate Garner.
Headlining Glastonbury, 1990
Sinéad was the queen of 90s normcore. She looked achingly cool headlining Glastonbury in 1990 wearing a black leather jacket with the sleeves pushed up, a Fat Slags white tee tucked into washed out high-waisted denim, and dark teashades. The Fat Slags was a raunchy comic strip launched in 1989 portraying two women who were constantly getting pissed, eating chips and shagging random men. This was Sinéad’s staple uniform; simple, unadorned, effortless. It endures in part because it’s so easy to recreate, but few could carry it off with the same aloof edginess as she could.
At the Annual Billboard Music Awards, 1990
Sinéad repped Ireland at LA’s first ever Billboard Music Awards in 1990 wearing a chunky pendant necklace depicting the Irish flag. She came up to accept her win in a hooded black jacket that resembled the robe wrestlers wear when they get in the ring, taking home the award for Number 1 World Single for her hit Prince cover “Nothing Compares 2 U”. It was presented by Joni Mitchell, from one heartrending songstress to another.
At the MTV Video Music Awards, 1990
Sinéad won big at the 1990 MTV Video Music Awards, taking home awards for Video of the Year, Best Female Video and Best Postmodern Video. The 23-year-old beat the likes of Aerosmith, Madonna and Red Hot Chilli Peppers for “Nothing Compares 2 U”. She performed the song at the ceremony in another ode to 90s casual: a loose fitting white maxi dress she paired with Doc Martens and oval sunglasses. She put comfort first while suggestively exposing the black slip she wore underneath.
At Glastonbury, 1992
In another of her iconic 90s Glasto moments, Sinéad, who the press said referred to herself as “the Irish Princess Diana” wore a green tee with the sleeves rolled up and the words ‘Irish Princess’ scrolled across the front. She may not have been literal royalty, but she definitely secured her place as a fearless Irish icon, thanks to her music and outspoken nature as much as for her personal style.
This article was originally published on 10 October 2022 and has since been updated.