Jennifer Lopez’s Best Early-2000s Outfits, Ranked

Jennifer Lopez
Jennifer Lopez

When news broke that Jennifer Lopez would be paying tribute to the late Selena Quintanilla at the Billboard Latin American Music Awards on April 30, visions of early-2000s J.Lo looks came rushing back to us. Here, we’ve compiled a ranked guide to 11 of the triple-threat’s best looks from the first years of this century—from that Versace gown to that white headband.

11. J.Lo at the Dolce & Gabbana Ultimate Hollywood party, 2003
Lopez showed up to this party in a surprisingly demure outfit, which could explain why it’s seared into our brains.

10. J.Lo at the Nickelodeon Kids’ Choice Awards, 2004
There are so many trends in this awesomely 2000s outfit we aren’t sure where to start: the plastic mules, the sequined bolero, the off-kilter hat—leave it to Lopez to pile on all of them and not look absolutely crazy.

9. J.Lo at the MTV VMAs, 2001
This is what we’ll call quintessential J.Lo, especially during her Sweetface-fashion line days: A floppy hat, knee-high boots, and a pirate-meets-peasent kind of dress.

8. J.Lo at the Oscars, 2002
The gown may have been Versace, but it was way different from the other gown from the brand that we know all too well. Girly glam curls matched the über-feminine vibe of her look.

7. J.Lo at the Today show, 2001
Lopez wore this look to PERFORM on the Today show (yes, seriously!), promptly causing girls every where to ask their parents for a Juicy Couture tracksuit and Adidas shell-toe sneakers for their birthday.

6. J.Lo at the Gigli premiere, 2003
The movie may not have received the best reviews, but the Gucci dress she wore to the premiere definitely did. Showing up on Ben Affleck’s arm probably didn’t hurt.

5. J.Lo at the Golden Globes, 2004
Who can forget when a super-bronzy Lopez glowed at the Golden Globes in this orange Michael Kors gown? No wonder we named it one of the 10 moments in her red carpet history.

4. J.Lo at TRL, 2001
If you were a tween in the early 2000s, you rushed home right after school to watch TRL. J.Lo wore this pink track suit with one leg scrunched up (obviously), heels, and matching pink pageboy cap the day she appeared on the show with then boy band B2K.

3. J.Lo at the Oscars, 2003
During peak Bennifer time, Lopez chose a mint green Valentino gown for the 2003 Academy Awards. This is undeniably one the most gorgeous looks Lopez has ever worn on a red carpet.

2. J.Lo at the MTV VMAs, 2000
The singer wore some of her most J.Lo outfits during her relationship with Puff Daddy, one of our favorites being this crop top and low-rise two-piece number complete with matching headband. Those abs!

1. J.Lo at the Grammy Awards, 2000
Of course this takes first place! Lopez only changed dress codes as we know them when she showed up to the Grammy Awards in the Versace plunging-neckline gown 15 years ago. The crazy thing is the 45 year-old would look just as good in it now as she did back then.

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