There’s much ado about attending the Vanity Fair Oscars after-party these days, especially since it boasts a buzzier guest list than the Oscars proper. More importantly, unlike the awards show’s red carpet, where stars typically avoid taking fashion risks, A-listers come out swinging at the after-party. This year’s leg, for example, saw some of the nakedest, nippliest ensembles in the event’s history.

At the turn of the millennium, however, the famed party was only in its seventh year. And while attendees now know exactly how to steal the spotlight, back in the noughties, they were still playing it fairly low-key. Jennifer Aniston, however, walked the red carpet in what might be her most daring ensemble of all time.

Jennifer’s Plunging Number

On March 26, 2000, the Friends star made her Oscars debut in a classic black dress. Her floor-length satin number featured a halter neckline and flowy skirt. It was simple, by all means — except for one little detail. The dress featured a deep V neckline that dipped so low it almost showed her navel. It was a showstopper to be sure.

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Aniston clearly recognized she had hit her fashion sweet spot. In the following years, she made the plunging LBD her signature awards show style, wearing multiple iterations — all with similarly daring necklines.

A Moment For Her Choker

Anyone who studies red carpet fashion knows: a low-low neckline is the perfect opportunity to introduce a statement necklace. Aniston did just that, balancing out the revealing cut with a diamond-encrusted choker. It gave her little black dress the extra star power it needed for such a glamorous event.

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A Moment For Her Date

Her then-boyfriend Brad Pitt looked quite dapper himself, in a simple black tux. The traditional style was elevated, thanks to a satin lapel and necktie that perfectly matched Aniston’s dress.

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A few months after this outing, Hollywood’s it couple tied the knot in Malibu, California. They divorced five years later, but to this day, their red carpet moments are still the blueprint for couples dressing.