Twenty years later, Ben Affleck and Jennifer Lopez — or as the world knows them best, “Bennifer” — are officially back together for the long haul. Between their reunion in April 2021 and Affleck’s intimate bathtub proposal featuring a green-gem stone engagement ring and their intimate Vegas wedding, all eyes are on the Hollywood It couple. Aside from their epic love story, Lopez and Affleck have shown time and time again that their cohesive style is something to behold.
While Lopez is no stranger to delivering iconic fashion moments, like her green Versace dress at the 2000 Grammys or her Sean John crop top and low-rise denim combination at the VMAs that same year, Affleck’s look is also noteworthy. Their Y2K street style began with Lopez often sporting Juicy Couture velor tracksuits or flared jeans and heels and Affleck rocking graphic tees over long-sleeve shirts, short mirror shades and cargo pants. Affleck has always opted for simple basics to allow Lopez’s extravagant pieces to shine. And in their early days, that meant plaid newsboy caps, baby-blue cropped coats and fuzzy scarves for him. Together, they set off every 2000s trend we’ve ever wanted to recreate and then some.
Today, Affleck sticks to his mostly neutral palette and often experiments with texture (think velvet tuxedos and suede coats). We’ve seen them recently on the streets and at the Met Gala, mixing shades of brown and black and going for all-out glamor on red carpets for movie premieres. Ahead, scroll through all their style moments, starting with looks that will deliver a huge dose of fashion nostalgia and ending with their latest looks.
– Additional reporting by Hannah Weil McKinley