30 Iconic Bennifer Fashion Moments, From Y2K to Their Wedding

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

Jennifer Lopez and Ben Affleck in Paris
Getty | Pool LE FLOCH/TRAVERS

Jennifer Lopez and Ben Affleck in Paris

Lopez wore the ultimate 2000s combination on the couple's trip to Paris, choosing white low-slung flares, a baby-blue cropped shearling jacket, a plaid newsboy cap, and tinted sunglasses. Affleck, meanwhile, stuck to varying shades of brown.

Jennifer Lopez and Ben Affleck in Beverly Hills
Getty | Mel Bouzad

Jennifer Lopez and Ben Affleck in Beverly Hills

On a stroll in Beverly Hills in October 2002, the couple were a complete early aughts mood, from the baby-pink velour tracksuit to the baggy jeans and shades.

Jennifer Lopez and Ben Affleck in New York City
Getty | Mario Magnani

Jennifer Lopez and Ben Affleck in New York City

This his-and-hers fall 2002 style moment in Manhattan looks straight out of an editorial for a J.Crew catalog.

Jennifer Lopez and Ben Affleck at the "Daredevil" Premiere
Getty | Frederick M. Brown

Jennifer Lopez and Ben Affleck at the "Daredevil" Premiere

Lopez was glowing in this Pucci gown at the "Daredevil" premiere in 2003. Affleck looked polished in a standard suit.

Jennifer Lopez and Ben Affleck at the Sundance Film Festival
Getty | Frazer Harrison

Jennifer Lopez and Ben Affleck at the Sundance Film Festival

Affleck's sunglasses cement this moment in our minds as the two showed off their winter wear in Park City, UT, at Sundance in 2003.

Jennifer Lopez and Ben Affleck in New York City
Getty | James Devaney

Jennifer Lopez and Ben Affleck in New York City

For an NYC date night in October 2003, Lopez dressed up in all-white satin, while Affleck dressed down in all black.

Jennifer Lopez and Ben Affleck in Paris
Getty | Pool LE FLOCH/TRAVERS

Jennifer Lopez and Ben Affleck in Paris

Shopping in Paris in April 2003, the couple subtly coordinated in tan blazers, though Lopez's Louis Vuitton bag and shades are the obvious stars here.

Jennifer Lopez and Ben Affleck at the "Maid in Manhattan" Premiere
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Jennifer Lopez and Ben Affleck at the "Maid in Manhattan" Premiere

At the "Maid in Manhattan" premiere in NYC in 2002, the two gave us bonafide Hollywood royalty vibes.

Jennifer Lopez and Ben Affleck at MTV's "TRL"
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Jennifer Lopez and Ben Affleck at MTV's "TRL"

Leaving "TRL," Affleck and Lopez were a whole winter 2002 vibe in denim and classic coats.

Jennifer Lopez and Ben Affleck at the 2003 Oscars
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Jennifer Lopez and Ben Affleck at the 2003 Oscars

For the 2003 Oscars, Lopez slipped into a now-iconic one-shouldered Valentino gown with chandelier earrings and Affleck wore a classic black tux.

Jennifer Lopez and Ben Affleck at the "Gigli" Premiere
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Jennifer Lopez and Ben Affleck at the "Gigli" Premiere

For the "Gigli" premiere in 2003, Lopez stunned in a brown Gucci gown, while Affleck wore baby blue with his black suit.

Jennifer Lopez and Ben Affleck in Canada
Getty | Jeff Vinnick

Jennifer Lopez and Ben Affleck in Canada

While filming an interview in July 2003, the pair kept it cool and casual. We only wish Affleck had a tracksuit to match.

Jennifer Lopez and Ben Affleck in Canada
Getty | Jeff Vinnick

Jennifer Lopez and Ben Affleck in Canada

For a summer 2003 outing in Vancouver, Canada, Affleck chose a monochromatic palette, while Lopez went with a quintessential early aughts look in low-rise jeans and a belly-baring tank.

Jennifer Lopez and Ben Affleck at Blockbuster
Getty | Jeff Vinnick

Jennifer Lopez and Ben Affleck at Blockbuster

A very "stars, they're just like us" moment with Affleck in khakis, and Lopez in denim and heels at a Blockbuster Video in June 2003.

Jennifer Lopez and Ben Affleck in New York City
Getty | Arnaldo Magnani

Jennifer Lopez and Ben Affleck in New York City

For a December 2003 date in NYC, Lopez was all dressed up in a flowing coat and cognac boots, while Affleck stepped out in baggy jeans.

Jennifer Lopez and Ben Affleck in New York City
Getty | Arnaldo Magnani

Jennifer Lopez and Ben Affleck in New York City

Lopez and Affleck wore his-and-hers scarves for a December date night in NYC in 2003.

Jennifer Lopez and Ben Affleck in Beverly Hills
Getty | Ben-Ari Finegold

Jennifer Lopez and Ben Affleck in Beverly Hills

The zip-up hoodie under the blazer is classic early 2000s, as are Lopez's knee-high boots and mini skirt combo on a walk in LA in October 2002.

Jennifer Lopez and Ben Affleck Courtside in Los Angeles
Getty | Vince Bucci

Jennifer Lopez and Ben Affleck Courtside in Los Angeles

Both played it casual courtside at the Lakers game in 2003.

Jennifer Lopez and Ben Affleck at the "Marry Me" Premiere
Getty | Steve Granitz

Jennifer Lopez and Ben Affleck at the "Marry Me" Premiere

On a big night supporting Lopez's movie "Marry Me," Affleck developed his signature of wearing long black blazers, while Lopez's white lace dress from Giambattista Valli made the statement.

Jennifer Lopez and Ben Affleck at the "The Tender Bar" Premiere
Getty | Steve Granitz

Jennifer Lopez and Ben Affleck at the "The Tender Bar" Premiere

Affleck's classic black suit was the perfect complement to Lopez's show-stopping blue sheer dress from Elie Saab on the red carpet in Hollywood.

Jennifer Lopez and Ben Affleck at the "The Last Duel" Premiere
Getty | Arturo Holmes

Jennifer Lopez and Ben Affleck at the "The Last Duel" Premiere

In another Hollywood moment at "The Last Duel" premiere, the couple played with different textures. Affleck wore a velvet suit and Lopez opted for a brown spandex glitter set from Hervé Léger.

Jennifer Lopez and Ben Affleck in Madison Square Park
Getty | Gotham

Jennifer Lopez and Ben Affleck in Madison Square Park

Take a New York City stroll, but make it fashion. We love how Affleck's simple looks always give Lopez her chance to shine, especially in this Christian Dior coat and dress combo.

Jennifer Lopez and Ben Affleck at the 2021 Met Gala
Getty | Jamie McCarthy/MG21

Jennifer Lopez and Ben Affleck at the 2021 Met Gala

At the 2021 Met Gala, Lopez wore a Ralph Lauren feathered dress while Affleck went with a classic tux, proving brown and black can absolutely pair well together.

Jennifer Lopez and Ben Affleck in Midtown
Getty | Gotham

Jennifer Lopez and Ben Affleck in Midtown

With hints of tan in each look, the couple did winter altheisure right in New York City. In coordinating sneakers, Lopez opted for an all-white look and a pair of Oree New York City High V1s, while Affleck rocked a classic white and gray pair.

Jennifer Lopez and Ben Affleck after Global Citizen Live
Getty | Robert Kamau

Jennifer Lopez and Ben Affleck after Global Citizen Live

While Ben mixed midnight navy and black, Lopez went the ultimate NYC street style route with a Dolce & Gabbana "J Lo" T-shirt, ripped jeans, silver heels, and a black clutch of the same brand.

Jennifer Lopez and Ben Affleck in Midtown
Getty | Gotham

Jennifer Lopez and Ben Affleck in Midtown

These looks make us crave a monochromatic moment of our own. While Lopez took on brown in a suede and leather ensemble, Affleck stuck with an all-black look.

Jennifer Lopez and Ben Affleck at the Venice International Film Festival
Getty | Stephane Cardinale - Corbis

Jennifer Lopez and Ben Affleck at the Venice International Film Festival

Their relationship became red carpet official in the most grand way, with Lopez in a white satin gown from Georges Hobeika, complete with an embellished plunging neckline. Affleck wore a classic black tux.

Jennifer Lopez and Ben Affleck in New York City
Getty | Hollywood To You/Star Max

Jennifer Lopez and Ben Affleck in New York City

Together leaving "Jimmy Kimmel Live!," the couple played with accents of blue, with Lopez wearing a Max Mara coat layered over a Brunello Cucinelli ensemble and finished with a Valentino bag. Affleck opted to rock a blue button-down under a camel coat.

Jennifer Lopez and Ben Affleck in Beverly Hills
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Jennifer Lopez and Ben Affleck in Beverly Hills

Lopez opted for a fiery bohemian moment in this floor-length red halter maxi dress, completing the look with towering espadrille wedges, her Hermès crocodile cuff bracelet, and big silver hoop earrings. Meanwhile, Affleck kept it casual for a day of house hunting in a flannel, dark pants, and complementary colorblock sneakers.

Jennifer Lopez and Ben Affleck's Wedding

The couple finally made it to the altar 19 years after their first engagement, saying their "I Do's" at the famed Little White Wedding Chapel in Las Vegas. For the special day, Lopez wore two wedding dresses: a Zuhair Murad Spring 2023 long-sleeved gown with an off-shoulder neckline and a corset bodice, and an Alexander McQueen sleeveless white frock with a pleated skirt "from an old movie" that she's had for years. Affleck wore a white tuxedo jacket over black trousers.