The 32 Coolest Vintage Dresses Celebrities Have Ever Worn

vintage - kate moss, dua lipa — (Image credit: Getty Images)

In recent years, dipping into the sartorial archives has become a tried-and-true way for a celebrity to stand out on a red carpet—but it's not a new trend. Archival fashion has long been a beloved source of inspiration for stylists and stars alike, though vintage gowns have become fixtures at major events as more celebrities champion sustainable dressing.

From intentional, headline-grabbing callbacks to old dresses that a celebrity or their stylist found at random, these are the coolest vintage dresses ever to hit the red carpet.

Kim Kardashian, 2020 Vanity Fair Oscars After Party

This dress was apparently a gift to Kim Kardashian from Kanye West: it's the Lee Alexander McQueen “oyster dress” from the spring 2003 collection. According to Vogue, she had to lie down on the floor of the car to preserve the gown, but her entrance (and the iconic status of the dress) shut down the carpet.

Emma Watson, 'Harry Potter and the Half-Blood Prince' Premiere, 2009

Emma Watson has been a fan of vintage (and ethical fashion) for a while before other celebrities did. This was a vintage Ossie Clark gown and has that perfect mix of sweet and chic that the star is known for; it's considered one of her best red carpet looks.

Reese Witherspoon, 2006 Oscars

On the night she won an Oscar for Walk the Line, Reese Witherspoon wore a gorgeous Dior dress that was made back in 1955 (!). The soft, romantic, floral dress was a perfect choice for the ceremony; Witherspoon doesn't always wear vintage but apparently loves it.

Naomi Campbell and Law Roach, 2024 Cannes

Law Roach always has an eye for a stunning piece: here, he styles Naomi Campbell in the same Chanel dress that she wore on the runway in 1996 (with some modifications: she didn't wear a slip underneath this time and wore bigger hair and earrings). Talk about a before and after!

Mary-Kate and Ashley Olsen, 2019 Met Gala

The Olsens wear a ton of vintage clothing when they make the occasional red carpet appearance. This is vintage Chanel and shows how much the sisters were ahead of their time (it was a little more unusual to see vintage at the Met Gala in 2019) and, while they don't always dress to the theme, they always look wholly themselves.

Kate Moss, 1998 Cannes

Attending the Fear And Loathing In Las Vegas Cannes premiere with Johnny Depp, Kate Moss wore a simple vintage Jean Dessès dress (black, with feathery trim). According to British Vogue, when she did a design collaboration with Topshop she recreated this dress.

Winona Ryder, 2000 Oscars

Winona Ryder apparently loved this strapless gown: she wore it to a bunch of red carpet events before taking it to the Oscars with a headband and silk-lined shawl. Per British Vogue, it's a Pauline Trigère dress from the 1940s and is notable for its daring deep neckline in front.

Iris Law, 2022 Perfect Magazine LFW party

Iris Law (Jude's daughter) has an eye for vintage. This is actually a gown from Versace’s fall 2003 collection—so the dress is almost as old as she is—and it has a cool lineage. Christina Aguilera wore it for an ad campaign, and then Beyoncé wore it to the 2003 MTV Movie Awards.

Natalie Portman, 2012 Oscars

This red polka-dotted gown originated from the Christian Dior’s spring/summer 1954 collection; it's simple and stunning on Natalie Portman, whose Oscars style is always elevated and classic. Not long after, the dress sold for $50,000, in case you're curious.

Penelope Cruz, 2023 Met Gala

Wearing vintage Chanel from 1988 (alongside her fellow Met Gala co-chair Dua Lipa, who also wore a vintage piece from the brand), Penelope Cruz noted, “I am probably one of the biggest fans of Chanel and Karl in this world." It was fitting to the theme: “Karl Lagerfeld: A Line of Beauty."

Jennifer Aniston, 2020 SAG Awards

If this look feels familiar to you, it's because it's the evening Jennifer Aniston looked delighted to run into ex Brad Pitt (and won an award on top of that). This is actually vintage Dior by John Galliano, and she rocked the silk bias-cut gown to absolute perfection.

Julia Roberts, 2001 Oscars

This stunning black and white striped gown is from Valentino’s autumn/winter 1992 couture collection. Roberts said she tried on the dress the day before the ceremony and they didn't have to do a single alteration to it—it's one of her most iconic looks to date.

Kim Kardashian, 2022 Met Gala

This look turned a lot of heads, and wasn't an un-controversial choice for Kim Kardashian. If you're unfamiliar, this is the dress Marilyn Monroe wore to sing "Happy Birthday Mr. President" to JFK (the dress was based on a sketch by Bob Mackie). Kardashian could only wear it for a short time, as it's a historical artifact.

Bella Hadid, 2022 Cannes

Bella Hadid attended Cannes (for a screening of The Innocent) in this vintage Versace gown from their spring/summer 1987 collection. Hadid worked with Law Roach on the red carpet look, and the dress is actually 10 years older than she is. The mermaid shape was an absolute showstopper.

Zendaya, 2022 'Euphoria' Season 2 Photo Call

Zendaya is a well-known lover of vintage, so this black and white Valentino (previously modeled by Linda Evangelista on the 1992 runway) was an intuitive choice for her to celebrate the upcoming season of Euphoria. She was styled, as she so often is, by Law Roach.

Kate Moss, 2007 "The Golden Age Of Couture" Party

This stunning gold gown is Christian Dior vintage. Moss has been wearing vintage since the '90s and this shiny gown is considered one of her best vintage pieces ever. “I love vintage shopping; it’s my favorite thing," she told British Vogue. "I go in and I can feel it—there’s treasures in there."

Amber Valletta, 2022 Met Gala

This shiny gold, pleated gown (for 2022's "In America: An Anthology of Fashion" Met Gala) is apparently a 1980s design by Azzaro. Per Harper's Bazaar, Amber Valletta's stylist sourced it from LA-based boutique Aralda Vintage, which is the source of other a-list vintage.

Jennifer Lopez, 2006 Oscars

This olive green Jean Dessès gown on Jennifer Lopez dates all the way back to 1959. J.Lo is a frequent presence at the Oscars (and green is a particularly great color on her—see also the naval-grazing Versace gown she wore to the Grammys in 2000), and this architectural dress is an inspired choice.

Adwoa Aboah, 2019 GQ Men Of The Year Awards

This vivid lime green 2004 Gucci gown, part of Tom Ford's 2004 Fall ready to wear collection, is an absolute standout on Adwoa Aboah. The British model and mental health advocate is wearing the heck out of the dress, which in different lights looked an even richer emerald color.

Olivia Rodrigo, 2024 Grammys

This three-decade-old Versace is older than Olivia Rodrigo! Originally, the dress was worn by Linda Evangelista all the way back in 1995, who wore a blonde wig and accessorized with a matching bag; Rodrigo went with a simpler option, with hair down and minimal accessories.

Winona Ryder, 1994 Oscars

Winona Ryder, proving her love of vintage has spanned decades, wears this Lily et Cie dress at the 1994 Oscars. It's a flapper dress that feels reminiscent of a 1920s Great Gatsby style; what I love about it especially is that it's a little simpler than what you might see at the ceremony, but no less gorgeous.

Sydney Sweeney, 2024 Vanity Fair Oscar Party

What's awesome about some vintage dresses is that they also serve as a callback to the original red carpet context. This is actually Angelina Jolie's 2004 Oscars dress, which in and of itself was an homage to Marilyn Monroe's famous white dress. Sweeney said she was thrilled to wear "a piece of history."

Cardi B, 2019 Grammys

In my opinion, this is one of the most daring, fun things Cardi B has ever worn (which is really saying something). This Mugler dress is from their Fall 1995 Couture collection, and Cardi B is actually wearing her hair in the same way as the model originally did.

Dua Lipa, 2023 Met Gala

While most eyes were on Dua Lipa's necklace at the Met Gala (she was the first to wear Tiffany Co.’s new Legendary diamond, and it's over 100 carats), we also love the Chanel dress she's wearing. It was originally modeled by Claudia Schiffer for the Fall 1992 couture collection.

Adut Akech, 2022 Met Gala

Adut Akech, who is a South Sudanese-Australian model, is wearing a gown from Christian Lacroix's autumn/winter 2003 collection. It's incredibly intricate, with the emerald green contrasted by the light green detail and light blue ribbons at her waist.

Miley Cyrus, 2017 'The Voice'

Miley Cyrus has worn some incredible vintage looks, and this strapless gold beaded look (worn while she was filming The Voice) is by Bob Mackie, apparently dating back to the ’80s. Cyrus doesn't always go with something so simple and classic—but she's nailing it here.

Amal Clooney, 2019 The Prince's Trust Dinner

What do you wear to Buckingham Palace for a dinner to benefit the Prince’s Trust? Well, if you're Amal Clooney, a divine vintage gown from Jean-Louis Scherrer’s Spring 2007 Couture collection. It's Grecian and expertly constructed with a cape flowing behind her.

Kirsten Dunst, 2022 Oscars

Even though it looks red, this gown from Christian Lacroix's autumn/winter 2002 couture collection is actually a deep pink color. Dunst has actually favored vintage and even vintage Lacroix before, rewearing a white dress in 2004 and then again in 2017.

Cardi B, 2021 'Thierry Mugler : Couturissime'

Cardi B loves Thierry Mugler, and with good reason: its over-the-top glamour and intricate construction is very in keeping with her red carpet aesthetic. This gown is haute couture autumn/winter 1995; Cardi B, who had given birth a few months prior, called herself “Mugler Mami” on Instagram.

Zendaya, 2024 Green Carpet Fashion Awards

Here, Zendaya was co-chair of the Green Carpet Fashion Awards, so (as befitting the event) she wore a flapper-inspired vintage Roberto Cavalli dress from their Spring 2011 collection. Zendaya has often worn vintage, but this detailed gown is a special standout.

EmRata, 2022 Met Gala

This vintage Versace on EmRata is a feast for the eyes; it's from their Spring/Summer 1992 collection and was worn by iconic supermodel Yasmeen Ghauri. Like the original styling, EmRata wore her hair up and paired the gown with shiny shoes; the skirt's volume had deflated a little with age, but it's still as stunning as ever.

Dua Lipa, 2022 Grammys

Dua Lipa is an absolute icon for wearing this belted black gown from Gianni Versace’s Fall 1992 ready-to-wear collection (originally modeled by Chrissy Turlington)—even dying her hair blonde to complete the look and layering with a ton of gold jewelry. A modern iteration on a classic, perfectly executed.

Katherine’s a contributing syndications editor at Marie Claire who covers fashion, culture, and lifestyle. In her role, she writes stories that are syndicated by MSN and other outlets. She’s been a full-time freelancer for over a decade and has had roles with Cosmopolitan (where she covered lifestyle, culture, and fashion SEO content) and Bustle (where she was their movies and culture writer). She has bylines in New York Times, Parents, InStyle, Refinery29, and elsewhere. Her work has also been syndicated by ELLE, Harper’s Bazaar, Seventeen, Good Housekeeping, and Women’s Health, among others. In addition to her stories reaching millions of readers, content she's written and edited has qualified for a Bell Ringer Award and received a Communicator Award.

Katherine has a BA in English and art history from the University of Notre Dame and an MA in art business from the Sotheby's Institute of Art (with a focus on marketing/communications). She covers a wide breadth of topics: she's written about how to find the very best petite jeans, how sustainable travel has found its footing on Instagram, and what it's like to be a professional advice-giver in the modern world. Her personal essays have run the gamut from learning to dress as a queer woman to navigating food allergies as a mom. She also has deep knowledge of SEO/EATT, affiliate revenue, commerce, and social media; she regularly edits the work of other writers. She speaks at writing-related events and podcasts about freelancing and journalism, mentors students and other new writers, and consults on coursework. Currently, Katherine lives in Boston with her husband and two kids, and you can follow her on Instagram. If you're wondering about her last name, it’s “I go to dinner,” not “Her huge ego,” but she responds to both.