Twenty years later, Ben Affleck and Jennifer Lopez — or as the world knows them best, “Bennifer” — are officially back together for the long run. From their reunion in April 2021 and Affleck’s intimate bathtub proposal featuring a green-gemstone engagement ring to their intimate Vegas wedding, the Hollywood It couple have all eyes on them. Besides their epic love story, Lopez and Affleck have shown time and time again that their coordinated style is something to watch.

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 looks are also noteworthy. Their Y2K street style began with Lopez frequently sporting Juicy Couture velour tracksuits or flared jeans and heels and Affleck rocking graphic tees over long-sleeved shirts, tiny mirror shades, and cargo pants. Affleck has always opted for simple basics to allow Lopez’s outstanding pieces to shine. And in their early days, that meant plaid newsboy caps, baby-blue cropped coats, and fuzzy scarves for her. Together, they pulled off every 2000s trend we’ve ever wanted to re-create and then some.

Today, Affleck is consistent with his mostly neutral palette and often experiments with texture (think velvet tuxedos and suede coats). We’ve recently seen them mixing brown and black shades, both on the street and at the Met Gala, and going for all-out glamour on red carpets for movie premieres. Ahead, scroll through for all their style moments, starting with looks that will provide a hefty dose of fashion nostalgia and ending with their latest appearances.

— Additional reporting by Hannah Weil McKinley