15 Iconic Couples from the Late ’90s and 2000s

December 02, 2025 Cosmopolite
A man and woman in matching white jerseys labeled

The late '90s and early 2000s gave us celebrity couples that shaped pop culture in a way no era has done since. From Britney Spears and Justin Timberlake's matching denim looks to David and Victoria Beckham dominating every red carpet, these relationships were everywhere. Whether they were glamorous, chaotic or short lived, each one left behind photos and stories that still define the nostalgia of that time.

1. Britney Spears & Justin Timberlake, 2001

A woman and man pose on a red carpet wearing matching denim outfits; the woman is in a strapless denim dress with a jeweled choker and accessories, while the man wears a denim jacket, jeans, and a denim hat.

A young Britney and Justin arrive at the AMAs wearing their now-iconic matching denim outfits. The look became a defining moment of early 2000s pop culture.

2. Brad Pitt & Jennifer Aniston, 1998

A man and a woman stand close together on a balcony at night. The man leans on the railing with his head resting on his hand, while the woman leans back against him, both looking relaxed and thoughtful.

Brad and Jen were still Hollywood's golden couple when they were spotted at a Radiohead show, looking effortless and completely in sync.

3. Victoria & David Beckham, 1999

A couple in winter jackets and hats walk two Rottweiler dogs on a wet sidewalk, holding hands. The woman wears a shiny silver puffer jacket and a baseball cap; the man wears a dark jacket and beanie.

David and Victoria step out in coordinated all-black outfits, proving why they became one of the most stylish and influential couples of their time.

4. Jude Law & Sienna Miller, early 2000s

A man in a dark suit and a woman in a light blazer sit closely together in a crowded audience, both looking ahead with serious expressions. People seated around them are engaged in conversation or reading programs.

Jude and Sienna appear at an event during the peak of their bohemian It-couple era, when their style and chemistry made them instantly recognizable.

5. Ashton Kutcher & Demi Moore (mid-2000s)

A man in a black tuxedo and sunglasses holds hands with a woman in a pale pink, strapless gown. They are smiling and posing together on a red carpet at a formal event with

Ashton and Demi pose together during the height of their surprising and headline-making relationship.

6. Michelle Williams & Heath Ledger

A woman in a yellow dress and a man in a black tuxedo pose together at an outdoor evening event, both smiling softly. There are blurred people and greenery in the background.

Michelle and Heath attend an event during the period when the two were admired for their quiet, genuine connection and timeless style.

7. Johnny Depp & Vanessa Paradis

A man in a camo jacket and flat cap walks hand in hand with a woman in a purple shawl and heeled boots at night on a city sidewalk, with another man walking nearby.

Johnny Depp and Vanessa Paradis appear at a premiere during the height of their long relationship, known for keeping a low profile despite their fame.

8. Pamela Anderson & Tommy Lee

A man with tattoos and a woman with long blonde hair sit together at a casino blackjack table, both focused on the game. Drinks are on the table, and other people are visible in the background.

Pamela Anderson and Tommy Lee are spotted together during their most talked-about years, a relationship that mixed glamour, chaos and unforgettable public moments.

9. Reese Witherspoon & Ryan Phillippe

A man and woman stand close together, posing for a photo. The man has short curly hair and wears a dark coat, while the woman has blonde hair tied back and wears a dark jacket. They are outside at night with rain visible behind them.

Reese Witherspoon and Ryan Phillippe attend a red carpet in their early years together, looking young, polished and completely wrapped up in each other.

10. Carmen Electra & Dave Navarro

A groom in a black pinstripe suit and a bride in a white wedding dress and veil embrace and smile at the camera, standing in front of a floral backdrop decorated with white flowers and greenery.

Carmen Electra and Dave Navarro show up in full rock-star style, perfectly embodying the dramatic and edgy aesthetic of early 2000s pop culture.

11. Nicole Kidman & Tom Cruise

A woman in a sleeveless burgundy dress and a man in a green long-sleeve shirt pose together on a red carpet, surrounded by photographers and onlookers.

Nicole Kidman and Tom Cruise attend an event during the height of their marriage, looking polished and glamorous in true Hollywood fashion.

12. Orlando Bloom & Kate Bosworth

A man in a suit smiles while walking with a woman in a gray dress who is laughing and leaning on his shoulder. They appear to be at an event or party, surrounded by other people.

Orlando Bloom and Kate Bosworth pose together during their early relationship, capturing the soft, romantic aesthetic that defined many couples of the time.

13. Lindsay Lohan & Wilmer Valderrama

A man in a dark suit and a woman in a black, floral-patterned dress pose together, smiling, in front of a white backdrop with red and blue logos.

Lindsay Lohan and Wilmer Valderrama pose during the short but very public romance that defined a big part of early 2000s celebrity culture.

14. Jennifer Lopez & Ben Affleck (original Bennifer era)

A woman in a light beige dress and a man in a dark suit hold hands and smile at each other while walking indoors, with other people and a chandelier in the background.

Jennifer Lopez and Ben Affleck walk together during their original Bennifer years, a relationship that dominated tabloids and red carpets long before their reunion.

15. Leonardo DiCaprio & Gisele Bündchen

A woman in sunglasses and a dark sweater holds hands with a man wearing a black NBA t-shirt and headband as they walk through a wooded area.

Leonardo DiCaprio and Gisele Bündchen attend an event during their peak supercouple years, looking effortlessly stylish and perfectly matched.

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