Before she was the 26-year-old blond movie star collectsing her best-actress Oscar in her bubblegum-pink Ralph Lauren, one of the youngest in history to receive that statuette, Gwyneth Paltrow was a brunette school girl best known for being the daughter of Tony Award-winning actor Blythe Danner.
After making her screen debut as a teenager, it was a few years before Paltrow broke out with David Fincher’s Seven. Then came a high-profile relationship with co-star Brad Pitt, memorable performances in Emma, Sliding Doors, and Great Expectations, and her rise as a ’90s fashion icon.
Throughout that era and beyond, her tousled bob has been as obsessed over as her supremely casual red-carpet wardrobe, which ranged from effortless slip dresses and leopard-print coats to jeans, leather jackets, perfect white T-shirts, chunky knits, and Converse. And when she did go all out—in, say, a red velvet Tom Ford for Gucci tux for the 1996 VMAs, or in a knock-out Armani naked dress for the 1998 premiere of Shakespeare in Love? Well, then fashion history was made.
In honor of the Hollywood stalwart’s 53rd birthday, we present 33 stunning throwback photos from the first phase of Paltrow’s career—also featuring the likes of Kate Moss, Winona Ryder, Giorgio Armani, Liv Tyler, Leonardo DiCaprio, and Ben Affleck, as well as endless style inspiration.
Photo: Getty Images1/331985
Gwyneth Paltrow, aged 12, in a floral tea dress and white pumps, at a benefit at New York’s Studio 54 with her mother, actor Blythe Danner.
Photo: Getty Images2/331990
Now 17, she poses with her castmates on High, the TV movie that marked her screen debut.
Photo: Getty Images3/331991
A luminous, 19-year-old Gwyneth, with her brother, Jake, Blythe Danner, and her father, Bruce, at the LA premiere of Barbra Streisand and Nick Nolte’s The Prince of Tides, in which Danner co-starred.
Photo: Getty Images4/331992
With Danner on the set of Cruel Doubt, the NBC miniseries in which they starred as a mother and daughter at the center of a gripping mystery.
Photo: Getty Images5/331992
An angelic head shot for Cruel Doubt, featuring Paltrow’s natural brown hair.
Photo: Getty Images6/331993
At 21, with a bob and the classic ’90s combo of a white T-shirt, buttoned-up cardigan, and leather jacket, at the LA premiere of Flesh & Bone, the Dennis Quaid and Meg Ryan thriller in which Paltrow co-starred.
Photo: Getty Images7/331994
In a dark red lip and a turtleneck for the National Board of Review Awards in New York, with a 19-year-old Leonardo DiCaprio.
Photo: Getty Images8/331994
For her very first Oscars, Paltrow chose a strapless silver column gown and pearl choker, paired with a sequined bag.
Photo: Getty Images9/331995
Aged 22 and now a blond, Paltrow attends the New York premiere of her latest film, the James Ivory period piece Jefferson in Paris, in a silvery white slip.
Photo: Getty Images10/331995
At 23, twinning in straight-legged denim with her then-boyfriend and Seven co-star, Brad Pitt, at the LA premiere of Sigourney Weaver’s Copycat.
Photo: Getty Images11/331995
Fresh-faced and delightfully low-key, with Pitt at an after-party following a David Bowie show.
Photo: Getty Images12/331996
In Converse and a leopard-print coat for the LA premiere of Robert Rodriguez and Quentin Tarantino’s From Dusk till Dawn, while holding the hand of her publicist, Stephen Huvane.
Photo: Getty Images13/331996
Wonderfully casual at a New York screening of Fargo with Brad.
Photo: Getty Images14/331996
In a sequined white slip for the 68th Academy Awards with Brad, who was nominated for a best supporting actor Oscar that year for 12 Monkeys.
Photo: Getty Images15/331996
The pair at the premiere of Paltrow’s rom-com The Pallbearer, in their regular ’90s off-duty uniforms.
Photo: Getty Images16/331996
A simple black maxi dress for the premiere of Emma.
Photo: Getty Images17/331996
Loose shirting and yellow-lensed sunglasses for a stroll down Madison Avenue.
Photo: Getty Images18/331996
A historic fashion moment: Paltrow in her red velvet Tom Ford for Gucci fall 1996 suit at the MTV Video Music Awards in LA. Almost three decades later, it remains one of the actor’s most iconic ensembles.
Photo: Getty Images19/331996
With the late, great Giorgio Armani at a party held by the maison.
Photo: Getty Images20/331997
Aged 24 and on The Tonight Show with Jay Leno, discussing her engagement to Pitt. A few months later, the couple parted ways.
Photo: Getty Images21/331997
In all-black for the New York premiere party of David Fincher’s The Game, with the director himself.
Photo: Getty Images22/331997
A sleeveless neutral knit with leather trousers for the New York premiere of Blythe Danner’s The Myth of Fingerprints.
Photo: Getty Images23/331997
A 25-year-old Paltrow filming the Andrew Davis thriller A Perfect Murder in New York.
Photo: Getty Images24/331997
Posing with Ashley Judd in a floor-length black dress with sheer detailing at the 1997 Met Gala, a celebration of Gianni Versace.
Photo: Getty Images25/331998
A strappy black maxi dress and precise bob for the LA premiere of Great Expectations.
Photo: Getty Images26/331998
With her friends Ben Affleck and Liv Tyler at the premiere of their new film, Armageddon.
Photo: Getty Images27/331998
Paltrow and Winona Ryder on their way to the Golden Globes, in pared-back monochrome ensembles.
Photo: Getty Images28/331998
At a Beck concert after-party in New York with Kate Moss and Liv Tyler.
Photo: Getty Images29/331998
In the Armani sequined naked dress to end all naked dresses for the New York premiere of Shakespeare in Love, aged 26.
Photo: Getty Images30/331998
A sequined skirt and black knit for the LA premiere of Shakespeare in Love.
Photo: Getty Images31/331999
A Golden Globe win from her first nomination for Shakespeare in Love, dressed in a strapless ballgown.
Photo: Getty Images32/331999
In wispy tulle for the Screen Actors Guild Awards, where Paltrow won two statuettes, for best actress and best ensemble.
Photo: Getty Images33/331999
The Academy Awards followed, where Paltrow scooped best actress yet again, this time in cotton-candy pink Ralph Lauren. At 26, she became one of the youngest best-actress Oscar recipients in history.
