14 Celebrity Photos That Look Like They Were Taken in a Completely Different Decade
It’s not always easy to tell when a celebrity photo was taken. Some pictures from the 1960s could pass for recent Instagram posts, while certain modern magazine shoots look as though they came straight out of an old Hollywood archive. A pair of sunglasses, a haircut, or the right lighting can throw off the whole timeline. And then there are celebrities whose personal style seems to belong to several decades at once. Reddit has plenty of photographs that make guessing the year surprisingly tricky, including old snapshots that barely look dated and newer pictures with unmistakably vintage details. Here are 15 celebrity photos that could easily confuse anyone trying to place them in time.
Madonna Before the ’80s Even Started
A 1979 photo catches Madonna riding a New York City bus, looking like someone who could be heading home from a downtown concert today.
Nicole Kidman Steps Into the 1940s
Nicole Kidman wore a black gown and long white gloves at Vogue World Hollywood in 2025, with her carefully styled hair recalling the movie stars of the 1940s.
Paul Newman’s Sunglasses Could Be From Yesterday
Paul Newman attended the March on Washington in 1963 wearing oversized sunglasses that wouldn’t look unusual in a contemporary street-style photograph.
Sydney Sweeney Could Be a 1940s Movie Star
Sydney Sweeney’s 2025 Empire photoshoot features blonde waves swept to one side and makeup inspired by Veronica Lake, a familiar face in 1940s Hollywood.
Princess Diana Was Ahead of the Fashion Curve
Princess Diana wore a suit and tie in 1994, with the oversized tailoring and relaxed styling fitting right into the current revival of menswear-inspired fashion.
Margot Robbie Recreates 1960 Barbie
Margot Robbie arrived at the 2023 Barbie premiere in a black Schiaparelli dress with matching gloves, recreating the doll’s 1960 Solo in the Spotlight outfit.
Debbie Harry Could Walk Into a Modern Rock Club
A 1978 photograph of Debbie Harry and Joan Jett captures two punk musicians whose casual styling wouldn’t attract much attention at a rock venue today.
Aaliyah Was Dressing for 2026
Aaliyah’s 1990s style featured oversized clothing and sporty pieces that wouldn’t look unusual in today’s streetwear scene.
Audrey Hepburn’s Style Still Works
A 1958 photo of Audrey Hepburn captures her relaxed personal style, with an outfit that feels surprisingly current despite being photographed nearly seven decades ago.
Michelle Pfeiffer Looks Ready for a Modern Photoshoot
A late-1970s portrait of Michelle Pfeiffer has the straightforward styling and close-up composition of a modern celebrity photograph.
Drew Barrymore Could Be in a 2020s Editorial
Drew Barrymore’s 1995 portrait has the kind of casual styling and close-up composition that could easily appear in a current celebrity magazine.
Cher Was Already Dressing for the Future
Cher’s 1974 Grammy Awards appearance featured a Bob Mackie design and elaborate headpiece that would still fit into a modern celebrity fashion retrospective.
Julia Roberts Was Ahead of the Oversized Suit Trend
Julia Roberts wore oversized suits on several occasions in the early 1990s, embracing relaxed tailoring and menswear-inspired looks that would fit right into today’s fashion.
Jimi Hendrix Would Fit Right Into Today’s Fashion
A 1967 photograph captures Jimi Hendrix on London’s Carnaby Street, wearing the kind of bold, expressive fashion that contemporary musicians still draw inspiration from.