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.
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.
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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.
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.
Swipe through the gallery to see more of Britney Spears’ nostalgia-inducing street style of the ’90s and early ’00s.
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Britney Spears’ Iconic VMA Style Through The Years