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Ahead of her concert in Singapore, we celebrate the Happier Than Ever singer’s coolest style moments in the spotlight

At only 20, Billie Eilish has already established a reputation as a red carpet rule-breaker. Her wardrobe of daring, fashion-forward outfits remind us that she isn’t just another cookie-cutter popstar, and that it’s impossible to actually fit her style—or her music—into a box. From baggy get-ups to ballgowns, Eilish’s style evolution has seen her try it all, but always with an undercurrent of edginess, as expected of the Gen Z superstar. Below, see how the singer has incorporated some of fashion’s coolest names, including archival Raf Simons and if-you-know-you-know Japanese designers, to her most memorable ensembles.

Read more: Billie Eilish Will Perform at Singapore’s National Stadium on August 21

1. 2022 Met Gala

Eilish took on the theme of Gilded Glamour at the 2022 Met Gala by channelling one of the most daring dressers of the late 19th century: Alva Vanderbilt. Staying true to the fashions of the Gilded Age, Eilish’s custom Gucci look featured a corset and a bustle skirt, while the singer herself posed as dramatically as Vanderbilt had during her famous costume ball of 1883. The corset was especially symbolic on Eilish, who just a year prior had made headlines with her British Vogue cover in which she wore lingerie—a radical transformation from a singer who was known to hide her figure through her oversized outfits. Here, Eilish looks as bold and brash as the corset-wearing models of Vivienne Westwood’s punk-inspired runway shows.

Read more: Met Gala 2022: The Couples That Conquered the Red Carpet

2. 2022 Grammys

Wearing a look from a menswear collection is typical Eilish—and that’s what the singer did when she attended the 2022 Grammy Awards. The all-black Rick Owens ensemble she chose featured a cocoon coat with its collar hanging over the chest, which may well be the edgy designer’s take on a classic Cristóbal Balenciaga couture creation. Adding to the cool factor of her essentially genderless look, Eilish sported a pair of Matrix-style sunglasses and Rick Owens sock boots.

In case you missed it: Grammys 2022: Best Dressed Asian Celebrities on the Red Carpet

3. 2022 Oscars

Eilish doesn’t do femininity in a straightforward way. Sure, this custom Gucci gown is layered with ruffles and boasts the volume of a ballgown, but its shapelessness ultimately lends it an armour-like quality that’s not often seen on women on the red carpet. The design has much in common with those of Rei Kawakubo and Simone Rocha (one of whose puffy dresses Eilish also wore to SNL), two designers who subvert femininity and champion individuality through their collections. Of course, this gown had to come in black—all the better to match Eilish’s gothic, black-hair-and-pale-make-up look.

4. 2021 MTV Video Music Awards

Takahiromiyashita The Soloist is the last fashion brand anyone would expect Eilish to wear—much less know. And yet it was the cult Japanese fashion label’s roll-neck jumper that surprisingly made it to the red carpet when the singer attended the MTV Video Music Awards—a rare occurrence for a brand that is mostly collected by menswear obsessives. The piece made sense on Eilish, who has shown a penchant for baggy ensembles. She completed this one with a midi skirt and chunky oxford shoes, all in black to bring out her blonde mop of hair.

5. 2021 Met Gala

After resembling a vision of Marilyn Monroe on the red carpet, a blonde-haired Billie hit the Met Gala after-party in an outfit inspired by Grace Kelly, another Old Hollywood icon. Her Oscar de la Renta gown was a tribute to Kelly’s wasp-waisted white dress in the 1955 film To Catch a Thief, but of course Eilish’s ensemble came with a twist courtesy of its deep red hue, its matching sheer cape, and a thigh-high slit that revealed the singer’s dragon tattoo.

6. Variety 2021 Music Hitmakers Brunch

Burgundy proved to be a popular colour with Eilish in 2021. The singer tapped on Los Angeles fashion label L.A. Roxx for another custom, wine-dark look that we can be best described as athleisure taken to the extreme. The padded puffer coat offered Eilish something of a train on the red carpet, but for vintage collectors the real show-stopping piece was her shoes: a pair of Raf Simons Ruby Bunny Boots from his fall/winter 2014 collection.

7. ‘Happier Than Ever’ Album Release party, 2021

Eilish embodied the ultimate Gen Z It-girl when she appeared at her album release party with the most Y2K-driven outfit she could pull off. The rebellious superstar sported a Miaou corset with a lace bra peeking out—the sort of layering trick that you’d expect from a 2000s teen drama star—and a pair of strappy leather pants that a Hot Topic goth would have killed to own. She certainly looked cooler than ever.

8. 2020 Grammys

Most people’s idea of Eilish is still drawn from her Bad Guy era when she had neon green highlights in her hair—and fairly so, given that it was one of the wildest looks in celebrity history. Eilish worked her streaks in her favour at the 2020 Grammy Awards, where she opted for yet another oversized silhouette in green Gucci sequins, no less. The look was coordinated right down to her nails, which came in a similarly verdant hue and featured the brand’s GG monogram.

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