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12 Millennial Fashion Icons Gen Z Should Revisit

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Millennial-core is taking over wardrobes. Name a trend, any trend, in 2024 and it probably had its roots in the ’90s or noughties. Whether it be our childhood faves (jelly sandals, overalls), mall-core essentials (skinny jeans, thongs, slogan tees), or the indie sleaze outfits we wore to festivals and nightclubs, it’s all coming around in the fashion cycle. While millennials have endured the ridicule of Gen Z for our side parts and ‘chugy’ denim choices—we know you’d love to raid our wardrobes for some vintage Sass & Bide.

While there’s already a laundry list of trends from which you can pick and choose, if you want to be ahead of the curve, it’s vital you look back to the icons of the era. Even more fascinating is that most of them remain fashion icons to this day, proving that trends may change, but true style endureth. So, here, for your fashion millennial hyper-obsession, the icons you should be studying. But first…

What Is Millennial Fashion?

One can’t talk about millennial fashion without talking about skinny jeans. If you took one item and applied it to a generation, the skinny jeans trend was the 2000s. This pairs with a number of other trends from the era: ballet flats, cardigans, ‘a nice top’, vests and thongs. As for the designers, American designers like Calvin Klein, Marc Jacobs, Ralph Lauren and Tommy Hilfiger were ubiquitous among the celebrity set. Internationally, funky Brits like Stella McCartney and Vivienne Westwood, and visually loud Italians, like Roberto Cavalli, Versace, and Fendi dominated trends. Meanwhile, Chloe, headed by Phoebe Philo, lead the charge of the ‘boho’ crowd, while everyone owned an LV-logo printed bag. Australian fashion also had a significant moment internationally, with Sass & Bide, Zimmermann and Colette Dinigan making waves amongst the celebrity set.

However, surf and skate-adjacent brands, like Von Dutch, Juicy Couture and Ed Hardy were key to understanding what most of us wore on a day-to-day basis. Trucker hats and tracksuits, anyone?

Best Millennial Fashion Icons

Alexa Chung

British It Girls were our catnip in the noughties, and nobody worked harder as a Tumblr style icon than Alexa Chung. The English society girl and model always circulated a rock ‘n’ roll set, whether starring in music videos or dating Arctic Monkeys frontman Alex Turner. This clearly influenced her style, with Chung frequently repping various combos of denim, leather or lace. She was the queen of high-low dressing, effortlessly pairing Hunter gumboots with designer shorts and a thrifted top.

Sienna Miller

If there is one person on this list closest to the author’s personal favourite, it’s Sienna Miller. The Queen of ankle boots, curtain bangs and bohemian red carpet-wear, Miller successfully captured all the sartorial desires of cool millennial women. (Yes, trying to wear dresses over your jeans was cool…)

Mischa Barton

If there was a queen of ‘jeans and a nice top’, it was Mischa Barton. Barton, and Marissa, her character on The OC, were looked to as key inspo for boho-partywear. Sparkly top, handkerchief hem, maybe some Keds? You’re all set.

The Olsen Twins

From beloved child stars, to sassy Met Gala attendees, to The Row powerhouses, the Olsen Twins have been at the forefront of style for millennial women for actual decades. Back in the noughties, the Olsen Twins underwent their tween icon-to-independent adult woman transition, and their perception shift was largely driven by fashion. With a clear love of the game, they were masters of layering and refusing to bend their personal style too far for a Met Gala theme. Now, the twins dialled back their eccentricity to to create The Row—one of the most lusted-after brands of the 2020s. If anyone knows what we’ll be falling over to buy next, it’s these two creative geniuses.

Rachel Zoe

Move over, Law Roach. The first major celebrity stylist to achieve celeb status in her own right was Rachel Zoe. She styled the likes of Nicole Richie (who should be on this list, but we’re including Zoe instead), Cameron Diaz, Kate Hudson, Anne Hathaway and more. She had her own TV series, The Rachel Zoe project, which she parlayed into a website and lifestyle brand, The Zoe Report, and, well, she basically pioneered the entire millennial-core aesthetic. Thanks, Rachel!

Rihanna

There was not one more influential haircut in the noughties than Rihanna’s ‘Umbrella’-era bob. In 2007, the singer cut her long hair into an asymmetrical bob, forcing women all over the world to imitate (and, dare we say, regret) the style. While this wasn’t Rihanna’s last trend-starting haircut, it was possibly the most significant.

The Gossip Girl cast

A key discourse of millennial girlhood was: Are you a Blair or a Serena Blair Waldorf, played by Leighton Meester, was the preppy, headband-wearing, designer queen. Blair was the bohemian, beach girl who could find a vintage bargain better than Carrie Bradshaw. Every millennial girl could see themselves in one of these two icons—with the occasional Jenny in the mix.

Katie Holmes

If there was ever a cardigan moment that lives in our mind rent free, it’s the sexy cardi pioneered by Katie Holmes. Holmes leans towards minimal and timeless pieces, which is why she can still wear them in 2024 and be the subject of our wardrobe envy.

Dita Von Teese

As a person who emulates a bygone era of style, few would associate her with millennial dressing. However, burlesque performer Dita Von Teese certainly shaped a certain section of style during this time, championing bustiers, pencil skirts and lingerie. As a rule, one could say lingerie peaked in the noughties, thanks to the Victoria’s Secret fashion show and celebrity driven campaigns by Agent Provocateur. In Australia, brands like Wheels & Doll Baby, and lingerie chain Honey Birdette each riffed on the trends put forth by Dita. While Dita’s vintage style is not currently on the millennial-core agenda, we could be seeing more of this in the coming years.

Carrie Bradshaw

If there’s one style icon that represents the noughties, it’s Carrie Bradshaw. (And, by extension, Sex And The City designer, Patricia Field.) Carrie’s style represents the eclectic ‘stylists’ of millennial-core. (It’s one thing to wear an outfit, it’s another to put that belt, with those shoes, right?!) By the time the first Sex And The City movie came out in 2008, anything worn by Carrie was expected to trickle down to the masses overnight. The movie hadn’t even come out before paparazzi snaps of Carrie in Dior gladiator heels caused mass hysteria.

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