Vintage fashion is making a bold comeback, thanks to today’s celebrities. With a nod to the iconic styles from the 1920s to the 2000s, these stars are proving that classic designs never truly go out of style.
From Old Hollywood glamour to Y2K cool, celebs of all kinds are reinterpreting trends from decades past, blending nostalgia with personalised flair.
Whether it’s a red carpet moment or street-style inspiration, these looks celebrate the enduring appeal of retro fashion, showing us that timeless elegance and old-school vibes can still feel fresh, relevant and utterly chic.
Celebrity nods to vintage fashion
Lily Collins
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Celebrating beloved ’60s hallmarks with a modern twist, Lily Collins captured the glamour of the Youthquake Revolution at the 2019 Met Gala with her white Giambattista Valli Haute Couture gown. Featuring a voluminous silhouette, ruffled bodice, and dramatic train, the Emily in Paris star truly embraced the romantic elegance of the era. A towering bouffant hairstyle adorned with delicate flowers oozed retro sophistication, while bold lavender eyeshadow added a striking, mod-inspired edge.
The Princess of Wales
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Whatever the Princess of Wales wears, she always looks effortlessly regal and impeccably stylish, and the striking hot red Alexander McQueen number she donned for 2023’s Royal Ascot was no exception. Embracing the ethereal glam of the 1970s the loose-fitting dress featured flowing fabric and a plunging neckline. Paired with a matching Philip Treacy hat, the look exuded a stylish take on bohemian elegance, reminiscent of the decade’s love for floaty, romantic silhouettes.
Winnie Harlow
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Daring to revive love for the double denim look at the F1 Grand Prix of Las Vegas on November 23, 2024, Winnie Harlow’s paid homage to a classic ’90s trend with an ’80s twist. Her oversized, boxy Louis Vuitton windbreaker jacket paired with matching jeans echoed 80s silhouettes, while silver cowboy boots added a playful Western flair. Proving the enduring appeal of classic denim, the model’s circuit-side ensemble successfully blended nostalgic fashion with a modern edge.
Jennifer Lopez
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Shining brighter than a diamond – and perhaps looking a little like one too – Jennifer Lopez’s look at the 2019 Met Gala wasn’t just a nod to 1920s flapper glamour; it positively screamed it. Fully embracing the evening’s camp theme, J.Lo stunned in a shimmering silver Atelier Versace gown with a plunging neckline and daring slit, radiating the over-the-top opulence of the Roaring Twenties. Topping it all off was a beaded headpiece inspired by iconic cloche hats, a hallmark of any true flapper, and a dazzling Harry Winston necklace featuring a 65.32-carat purple sapphire, cementing her as the night’s most sparkling star.
Lizzo
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Less Cockney Pearly Queen and more Coco Chanel, Lizzo’s lavish look at the 2023 Met Gala paid homage to the fashions of the 1920s and 1930s – an era when the French designer redefined elegance with pearls as her signature. Lizzo’s black silk dress, adorned with striking pearl embellishments, recaptures the opulence of the Jazz Age while nodding to Chanel’s timeless aesthetic. What’s more, with pearl bracelets galore, pearl-accented ankle boots, and a classic updo, Lizzo unquestionably nailed 1920s sophistication in style.
Christina Hendricks
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Ah, 1930s fashion – a decade of utility and understated sophistication defined by bias-cut dresses, structured shoulders, peplum jackets, and Mary Jane shoes. Blending this approach of practical style with vintage charm was Christina Hendricks at the 2021 Veuve Clicquot Polo Classic, who beautifully embodied the decade with a navy and white checked dress with a wide lace collar, waist tie, white bowler hat, black T-strap block heels, and a woven handbag. She completed the look with soft curls, minimal jewellery and her signature bold red lip.
Kerry Washington
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Who doesn’t love a bold splash of neon? The eighties certainly did, with the early part of the decade practically awash with it. Clearly, Kerry Washington is also a fan with her nod to ’80s power dressing in luminescent green as she stepped out in New York City to promote her series UnPrisoned. Featuring sharp tailoring and pointy shoulder pads, she effortlessly blended retro influences with a modern, playful twist.
Kim Kardashian
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Some may argue that Kim Kardashian is to this generation what Marilyn Monroe was to hers: controversial, unapologetic, and undeniably beautiful. Perhaps that’s why the reality star-turned-entrepreneur chose to channel the screen icon at the 2022 Met Gala, stepping onto the red carpet in Marilyn’s legendary, glittering and curve-hugging “Mr. President” gown.
Like many of Kim’s fashion choices now, the dress’ debut caused a bit of a to-do for Marilyn back in 1962, when she wore it to serenade President Kennedy on his birthday. While a platinum-blonde Kim wore a replica of the gown for most of the event, she was granted special permission to wear the fragile original for just a few minutes on the red carpet, ensuring her homage to classic Hollywood was paid.
Cynthia Erivo
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Cynthia Erivo’s look at the New York premiere of Wicked on November 14, 2024, was a masterclass in blending 1950s elegance with a contemporary twist. Her custom Christian Dior ensemble featured an almost gingham-style print, with a tailored jacket layered over a lustrous silk shirt and a dramatic flared skirt. The 1950s-inspired silhouette, paired with modern details like pointed heels and bejewelled razor-sharp nails, made her look both timeless and refreshingly unique.
Jessica Chastain
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Throwing herself wholeheartedly into 1960s Italian glamour at the Gucci RTW Spring 2025 show during Milan Fashion Week, Jessica Chastain wowed in her off-the-shoulder daisy-print dress, reminiscent of a young Brigitte Bardot. Styled with Gucci Signoria slingbacks, oversized black sunglasses, and silver jewellery, the actress completely pulled off the playfully chic spirit of La Dolce Vita.
Ashley Park
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While Ashley Park’s flared jeans paid tribute to the iconic bell-bottom trend of the disco era, the Emily in Paris actress’ triple-denim ensemble, featuring a Versace Medusa ’95 corset top and oversized blazer, nodded to the bold all-denim looks of the ’90s. The striking look, which she wore for her appearance on Good Morning America on September 17, 2024, seamlessly slayed retro influences from the 1970s and 1990s.
Lily-Rose Depp
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With her pink sequined Chanel ensemble – featuring a strapless crop top and matching skirt with black accents and floral embellishments – Lily-Rose Depp’s look at the 2021 Met Gala wowed as a deconstructed reinterpretation of the classic 1960s twin set. Blending vintage inspiration with her youthful look, the actress delivered the spirit of the ’60s youthquake revolution for a new generation.
Anne Hathaway
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Looking as though she’d just stepped out of Studio 54, Anne Hathaway dazzled at the 39th Film Independent Spirit Awards in a white sequinned Valentino jumpsuit, channelling the glamorous trends of 1970s disco fashion. The wide-leg silhouette and corseted bodice, adorned with crystal embellishments, perfectly captured the era’s iconic style. Her dark brown locks, styled in relaxed waves with a wispy fringe, added a touch of carefree ’70s chic, completing her on-point homage to the decade of nightlife glamour.
Lady Gaga
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Delivering a pint-size portion of 1940s Hollywood glamour to the 75th Venice Film Festival, Lady Gaga brought an iconic pin-up style that even Betty Grable would be impressed by. Showing off her platinum pin-curled updo paired with a bright red lip, bold brows, and a classic cat-eye, she wore a Jonathan Simkhai cocktail dress and black pumps to perfectly capture the vintage aesthetic.
Halle Bailey
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Halle Bailey’s look at the 2024 BET Awards embraced the edgy minimalism and cyberpunk influences of the late ’90s – popularised by blockbuster hits like The Matrix and Blade. The star of Disney’s Little Mermaid truly wowed in the backless black halter-neck gown by Avellano. With its wet-look leather and liquid-like gloss, she perfectly captured the decade’s rebellious and sultry, metallic allure.
Nicole Kidman
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Stepping out at the Queen of the Desert premiere during the 65th Berlinale Film Festival, Nicole Kidman turned heads with her masterful nod to 1970s bohemian fashion. Her white Valentino Haute Couture gown, adorned with daisy appliqués and flounced cuffs, channelled the free-spirited, romantic aesthetic of the era, and kept her strawberry blonde hair loose and soft, with natural makeup to complete the boho-glam vibe in effortlessly timeless style.
Gigi Hadid
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Walking the red carpet at the Deadpool & Wolverine premiere on July 22, 2024, Gigi Hadid looked every bit like the late ’90s to early 2000s fashionista. Her custom yellow Miu Miu bandana-style bandeau top and low-rise, knee-length skirt brightly channelled the trends of the Y2K era, while her slicked-back, gelled hair, accented with a dramatic quiff, could be a salute to decade-defining icons like Gwen Stefani. Further evoking the early “aughts” edginess were her super chunky accessories, including bangles, a wide belt, dangly earrings and a double-looped chain, perfectly capturing the carefree, statement-making vibe of the time without looking like a fancy dress costume.
Dita Von Teese
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Always one to bring a touch of class to any event she attends, Dita Von Teese, with her trademark alabaster skin and red lip, donned her staple black gloves, gold earrings, and signature quiff, as she arrived at the Crown to Couture exhibition launch at Kensington Palace. Renowned for her love of the 40s and 50s Hollywood glamour, the burlesque sensation didn’t disappoint in a form-fitting black Jenny Packham gown with gold beaded leaf detailing, statement shoulder pads, and a sleek full-length skirt, fully embodying the era’s cinematic elegance.
Zendaya
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Maybe Zendaya’s (or her stylist’s) love of the eighties movie classic Working Girl inspired this empowered wardrobe choice for the actress’ appearance on Jimmy Kimmel Live in April 2024. Channelling the Melanie Griffith aesthetic with a modern edge, Zendaya’s version of the classic grey suit jacket is contemporarily oversized, making it perfect to wear as a dress. Paired with a crisp white shirt, monochrome tie, polka dot pocket square, and white heels, the look nearly winks at the tailored silhouettes that defined women’s professional glamour in the 1980s.
Lindsay Lohan
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Proving that like a fine wine, Lindsay Lohan’s style has got better with age, the Mean Girls actress dazzled at the Michael Kors Spring/Summer 2025 show with her sleek salute to 1990s minimalism. Echoing the decade’s iconic understated elegance, epitomised by slinky, figure-skimming dresses, Lindsay’s grey satin-charmeuse slip gown wowed as an effortlessly chic throwback to ’90s fashion, which she paired with a slate grey wool melton coat featuring a faux fox collar.
Gisele Bündchen
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Gisele Bündchen looked every bit the Victoria Secret’s Angel when she dazzled at the 2023 Met Gala in a Chanel archival gown that paid homage to 1920s Art Deco design. The slim-fit white silk tulle dress featured vertical sequined stripes, evoking the geometric elegance of the era. Paired with a dramatically oversized feathered cape, the vintage glam look was a successful nod to the opulence that defined the roaring twenties, not to mention her “angelic” modelling career.
Ariana Grande
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Ariana Grande’s look on The Tonight Show Starring Jimmy Fallon channelled 1950s and 1960s elegance, reminiscent of Audrey Hepburn’s timeless style. The pint-sized pop star’s black Balmain dress, adorned with white rose-shaped buttons and a flared circle skirt, perfectly captured the poised sophistication of the era. The singer paired the dress with sheer tights, white Jimmy Choo heels, and her dedication to the charmingly retro getup even saw her break free of her trademark towering ponytail.
Billie Eilish
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Seemingly not content with just rocking an early 2000s sk8ter girl aesthetic, Billie Eilish went the whole hog and turned this late summer LA look into a homage to the one true, iconic pop-punk princess herself – Avril Lavigne. With her white graphic T-shirt, baggy jeans, loose tie and wide trainers, the multi-award-winning singer has completely captured the rebellious spirit of Y2K fashion.
Florence Pugh
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Florence Pugh’s bold nod to 1980s fashion wowed at the We Live in Time screening on September 9, 2024. Her sheer black lace Christian Dior gown, styled with a black bralette, high-waisted briefs, and a cinching leather belt, channelled the daring, iconic looks of Cher from the era. Elevated by platform heels, loose waves, natural makeup, and her signature nose ring, Florence added her own modern twist to the drama of ’80s glam.
Bella Hadid
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Channelling a decade when exaggeration defined sophistication, Bella Hadid looked phenomenal in a monochromatic Flamenco-inspired Chanel dress from Karl Lagerfeld’s Fall 1986 collection to the “Chopard Loves Cinema” Gala Dinner in Cannes. The stripey design, with its ruffled skirt and statement balloon sleeves, perfectly captured the era’s love for extravagant silhouettes. The model topped off the look with just the right touch of glamour to suit the occasion: a dazzling diamond-encrusted choker and an oversized white hair bow.
Maya Jama
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Turning heads at the star-spangled Manchester-held MTV Europe awards in November 2024, Maya Jama revived a slinky – not to mention potentially sharp – piece of nineties fashion history as she paid homage to that dress – Elizabeth Hurley’s Versace “safety pin” dress. The daring gown, held together by oversized gold pins, became a cultural phenomenon following its 1994 debut at the premiere of Four Weddings and a Funeral, when the actress accompanied her then-boyfriend and star of the movie, Hugh Grant on the red carpet.
Diane Kruger
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Nodding firmly in the direction of the 1970s, Diane Kruger rocked the Chloé Spring-Summer 2025 with this leather-tastic. As a hallmark of the bohemian trends of the decade, Diane’s rich brown leather jacket, featuring subtle fringe, paired with a deep purple turtleneck jumpsuit, embraced the decade’s penchant for warm tones and layering, while the dangly gold jewellery, chain link belt, caramel leather bag, tinted shades and sparkling strappy heels, added all the finishing touches to her vintage-inspired look.
Emily Ratajkowski
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Capturing the mishmash glamour of the noughties with a modern, polished twist, Emily Ratajkowski stepped out at the Moet & Chandon Holiday Season Celebration in 2022 in a graduated pink, mauve, and burgundy ombre dress that featured intricate beading and velvet details, combining early 2000s hallmarks like a cowl neck and ultra-low back. And let’s not forget those gladiator-strap silver stilettos to complete the effect.
Rihanna
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What do you get when you cross 1930s Hollywood glamour with traditional Chinese artistry? Rihanna’s Met Gala look – in which she seamlessly blends Eastern craftsmanship with Western vintage style, underscoring her unparalleled fashion prowess. The breathtaking canary-yellow Guo Pei cape gown – adorned with intricate embroidery and a dramatic train, was paired with a diamond choker, sleek hair, and an off-shoulder fur stole, evoking opulence worthy of silver-screen icons.
Cate Blanchett
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Is that Cher circa 1987? No, it’s Cate Blanchett, stealing the show with her unapologetically ’80s-inspired look at the 2024 Albie Awards. Draped in a sparkling black Louis Vuitton cape-style top and sleek leather trousers, the Hollywood A-lister brought the bold attitude of the decade’s fashion to life, with her edgy mix of sequins and sharp tailoring that perfectly channelled the rebellious glamour of ’80s rock culture.
Kris Jenner
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Kris Jenner isn’t one for bold colours and brash prints, which is why this understated 60s mod-inspired mini-dress is the ideal choice for her. Featuring a crisp white Peter Pan collar and oversized cuffs with charming black bows, the Momager teams the stylish retro-look dress with black tights and ankle boots for a minimalist and sophisticated ensemble that would make Twiggy proud.
Miley Cyrus
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With this nineties grunge look, Miley Cyrus’ sheer black, figure-hugging dress that ends just below the knees, pays homage to Kate Moss’s infamous see-through slip dress and her iconic “heroin chic” aesthetic. Appearing at Radio City Music Hall in New York City 2022, the singer teamed the almost see-through dress with casual, white-strap Chanel sandals.
Topping the look off (quite literally), Miley showed off her two-tone platinum blonde and brown hair, rounding out a look that blends ’90s minimalism with early 2000s edginess for a bold nostalgic statement.
