Brad Pitt and Jennifer Aniston’s top fashion moments of the ‘90s and early ‘00s

The former couple had some noteworthy looks

UPDATED JANUARY 22, 2020 3:58 PM ESTJAN 22, 2020, 3:58 PM EST

It’s been more than ten years since Brad Pitt and Jennifer Aniston separated, but their recent rendezvous at the Golden Globes and then again at the Screen Actors Guild Awards (SAG) literally broke the internet (according to SEMrush 61.33% of tweets mentioning Brad and Jen were positive).

Being we’re on the hot topic of all things Brad and Jen (BREN?) we’re taking a walk down memory lane to relive some of their most stylish looks of the 1990s and early 2000s. The former couple was Hollywood’s most sought and never failed to give the public something to talk about when at every red carpet event, movie premiere, and even when randomly spotted on the street.

Scroll through the gallery to see some of our favorite Brad and Jennifer style moments circa 2000.

Hats + Sunnies

The ex-lovers kept matching to a minimal by stepping out in different hats and dark sunglasses.

Neutrals for the win

The actors made a strong statement for sharp suiting, monochrome, and neutrals when they stepped in head-to-toe white and khaki ensembles.

Jacket weather

The former couple took another mismatching matching approach by pairing up with button-up jackets.

Back in black

The big-screen performers opted for darker garments with Brad rocking a pinstripe suit and Jen an edgy leather look.

So 2000s

The Benjamin Button star was so 2000s in slouchy denim, an untucked button-up shirt, and a leather sports coat. Meanwhile, Jen looked cool and effortless with a low-rise hem and basic tank top. Jennifer Aniston and Brad Pitt fashion

Hollywood’s IT

The actors showed up to a red carpet event exuding So-Cal vibes with Brad’s long shaggy hair and Jen’s “I woke up like this” beach waves.

Red carpet-ready

The hot couple had all eyes on them at the 2004 Emmy Awards. The Once Upon A Time in Hollywood actor wore a black Tuxedo while Jen slipped into a glam embroidered gown.

Fashion stars

We’re not sure what Brad’s doing here, but we do know he was into sporty sunglasses and slouchy suits. Jen, on the other hand, was experimenting with textured hair.

Too cool for...everything

The Along Came Polly actress kept cool with a full black outfit as Ben rocked a sleek suede jacket.

Head-to-toe-black X 2

Jennifer turned heads in a sexy slip dress, while her beau at the time stole the show in all black.