Britney Spears’ Best Street Style of the ’90s + Early ’00s – Footwear News

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In 1998, when Britney Spears was just 16 years-old, she released “…Baby One More Time” — and the rest, as they say, is history.

Spears’ cultural influence is still strong today, but the late ’90s and early ’00s could be called the “age of Britney.” The pop star, now 38, released a string of earworms throughout the era, often accompanied by attention-grabbing music videos.


Britney Spears, disney world, bucket hat, stuffed animals, pink t shirt, khaki pants, sneakers, Britney Spears at Walt Disney World, Orlando Florida, USA - 15 Jun 1999Britney SpearsBritney Spears at Walt Disney World, Orlando Florida, USA - 15 Jun 1999

Britney Spears in khaki pants and sneakers on a trip to Disney World in Florida, June 15, 1999.

CREDIT: Larry Marano/Shutterstock

Given her enormous popularity, Spears became a regular tabloid fixture — which means many of her street style looks are captured for eternity. With chunky sneakers, velour sweatsuits and wedge flip-flops galore, the A-lister’s outfits will hit you with a wave of nostalgia.

In particular, chunky sneakers were a huge favorite of the singer’s. She modeled the Skechers Energy, which was re-released earlier this year, in 1999. So-called dad shoes have been hot for the past few years, but they were also a must-have for every teen of Spears’ era — often teamed with track pants or low-rise jeans.


Britney Spears, crop top, yoga pants, chunky sneakers, street style, celebrity style, dad hat, no bra, braless, abs, BRITNEY SPEARS ON SUNSET DRIVE, LOS ANGELES, AMERICA - 13 OCT 2002Britney SpearsBRITNEY SPEARS ON SUNSET DRIVE, LOS ANGELES, AMERICA - 13 OCT 2002

Britney Spears wears a crop top, yoga pants and chunky sneakers in Los Angeles, Oct. 13, 2002.

CREDIT: Shutterstock

Another favorite shoe of Spears’ was the high-heeled flip-flop. She often teamed her rainbow-striped flip-flops wedges with minidresses and denim shorts in the summer months. While the silhouette has been much derided in recent years, it’s back in vogue now, thanks to a new wave of “It” girls like Rosie Huntington-Whiteley, Kim Kardashian West and Emily Ratajkowski.


Britney Spears, tank top, bra, rosary, wedge flip-flops, legs, arms, BRITNEY SPEARS AND KEVIN FEDERLINE BUYING AND XBOX CONSOLE, CALIFORNIA, AMERICA - 27 AUG 2004Britney SpearsBRITNEY SPEARS AND KEVIN FEDERLINE BUYING AND XBOX CONSOLE, CALIFORNIA, AMERICA - 27 AUG 2004

Britney Spears wears flip-flop wedges out and about with Kevin Federline in Los Angeles in August 2004.

CREDIT: Shutterstock


Britney Spears, minidress, flip-flop wedges, heeled flip-flops, celebrity style, BRITNEY SPEARS SHOPPING, LOS ANGELES, AMERICA - 31 AUG 2004

Britney Spears in flip-flop wedges and a striped minidress in Los Angeles, Aug. 31, 2004.

CREDIT: Shutterstock

The “Toxic” hit maker was also a huge fan of Juicy Couture’s velour sweatsuits, which also found popularity among stars like Paris Hilton, Pamela Anderson and Madonna.


Britney Spears, velour sweatsuit, juicy couture, abs, chunky sneakers, celebrity style, BRITNEY SPEARS SHOPPING ON SUNSET PLAZA, WEST HOLLYWOOD, AMERICA - 14 FEB 2003Britney SpearsBRITNEY SPEARS SHOPPING ON SUNSET PLAZA, WEST HOLLYWOOD, AMERICA - 14 FEB 2003

Britney Spears goes shopping in Los Angeles clad in a blue velour Juicy Couture sweatsuit and chunky sneakers in February 2003.

CREDIT: Steve Levy/Shutterstock

Swipe through the gallery to see more of Britney Spears’ nostalgia-inducing street style of the ’90s and early ’00s.

Want more?

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