WWD Report Card: The Look of Bennifer

Everything old is new again — yes, Bennifer is back. The “It” couple of the early 2000s seems to have reconciled, which naturally deserves a look back at their best style moments.

Jennifer Lopez and Ben Affleck at the premiere of “Gigli.” CHRIS POLK/AP

In their red carpet debut as an engaged couple at the premiere of the cult classic “Gigli,” Bennifer looked equally tanned and glammed. Lopez, in a naval-grazing brown Gucci by Tom Ford gown and pink diamond engagement ring, was the poster girl for early 2000s red carpet movie star. And Affleck was doing his best to keep up, with a baby blue matching tie-shirt combo.

Ben Affleck and Jennifer Lopez at the premiere screening of “Daredevil”. Lee Roth/AP

Lopez, in Pucci, is very 2003 in her babydoll cut. Affleck, meanwhile, loses points for both of them with his white tie. She’s always been the fashion star; he was just there and, at times, he looked a bit uncomfortable.

Jennifer Lopez poses with Ben Affleckat the 75th Academy Awards, 2003. Hubert Boesl/AP

For the 75th Oscars, Lopez opted for a retro ’60s Jackie Kennedy-inspired Valentino gown with Harry Winston jewelry and matching foam green eye shadow, while her other half was channeling Brat Pack Vegas vibes with a deep tan and glossed hair. For us, this is an iconic moment that defined the Bennifer era.

Jennifer Lopez and Ben Affleck, 2002. The Mega Agency

This is them at their peak of Bennifer. The baby pink Juicy Couture tracksuit and tight half pony is basically golden fashion history. When he was part of Bennifer, Affleck always looked the part, even when dressing down, as seen here in a casual white button-down shirt and black slacks.

Ben Affleck are seen on the upstairs balcony of Lopez’s rental home in Miami, 2021. CGMIA/Mega Agency

In a minimal fashion crowd uniform, Affleck looks very timely in a black crew neck and black jeans. The beard and messy hair enhance his mature sexy look.

Jennifer Lopez and Ben Affleck are seen on the upstairs balcony of her rental home in Miami, 2021. v

Even in this daytime off duty summer dress, JLo still brings the fashion drama with style. The loose bun hairstyle is very appropriate and extremely flattering.

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