Brad and Jen's Most Stylish Moments Prove They Should Have Another Reunion — For Fashion's Sake

Published on Sep 23, 2020 at 2:37 PM

Jennifer Aniston and Brad Pitt, quite possibly the world's most beloved celebrity couple, were together from 1998 through 2005, and every now and then, people seem to get nostalgic about their relationship. That's because Brad and Jen still run in the same circles, bumping into one another from time to time, ultimately causing us to reminisce about some of their memorable moments.

In our eyes, those instances will always include their most stylish red carpet looks — we immediately picture Jen carrying a mini satin shoulder bag on one arm, holding Brad's hand with the other — and their relaxed getaway style. Plus, to this day, we still haven't come across a couple to coordinate any better in denim (sorry, Britney and Justin) and leather jackets.

Whether Jen was showing off a vintage gown at a movie premiere, with Brad shielding his eyes from the sun (aka Jen) in suave sunglasses, or the duo were walking down the streets of California, they always had on the coolest outfits — many of which we'd still wear today. Scroll down to look back on their wardrobes with us. Normally, we'd advise you to try to recreate these outfits with your SO, but come on guys, it's Brad and Jen. Some things just can't be done.

Just Look at Their Sunglasses and Footwear on Their First European Vacation Together

Jen Redefined the Meaning of "Golden" at the 1999 Emmys

Hopefully Brad put his sunglasses back on. You know what they say about staring directly at the sun.

Jen's Elegant Red Prada Gown and Satin Shoulder Bag Stole the Show at the Emmys in 2000

Brad kept it simple, letting his lady shine — she was nominated that year for outstanding supporting actress in a comedy (Friends), after all.

Brad's Purple Leather Was on Another Level at the Rock Star Premiere in 2001

Jen let him revel in the spotlight this time, opting for a simple slinky tank and skirt.

Jen Repeated This Look in 2003, but With Boho Accessories to Flow With Brad

A Casual Trip to the Movies Called For Groovy Jeans

Denim and Takeout? Yeah, We've Been There Too

Jen and Brad Went For Shades of Brown at the 2002 Emmys

Jen was glowing in vintage Christian Dior.

Their Leather Jackets Were Always on Point

Here they are wearing their best basics in 2000 at the Erin Brockovich premiere.

Every Bit of This All-Black Outfit Moment Was in Sync

Peep Brad's thin silver chain and Jen's silver tennis bracelet.

They Were California Cool With Loose Cargos and Brad's Beanie

They Packed the Most Casual Cover-Ups For Their 2005 Trip to Anguilla

When Brad Wore His Patchwork Denim, Jen Was Effortlessly Sexy in a Tank and Trousers

Jen's classic look still achieves the same vibes today.

When Jen Took the Plunge, Brad Was There in His Best Black Tie

Guess They Were Feeling a Neutrals Night

They kept things light in his and her power suits at The Mexican premiere in 2001.

Nothing Is More Classic Than Jeans, Black Boots, and Fall Sweaters

Like We Said, Leather Jacket Game = Strong

But get a load of Jen's furry purse! This look is classic 2000s.

They Certainly Knew What to Do While Accessorizing in the Fall

Shades clipped onto sweaters in favor of hats.

Jen Let Her Midriff Show and Brad Popped His Collar

They were coordinated in the subtlest of ways at the LA Fight Club premiere in 1999.

Jen's Vintage Chanel Dress Made Waves at the 2004 Emmys

You can't distract from this look, right Brad?

Jen's Lace Slip and Strappy, Minimalist Heels Would End Up on Best Dressed Lists Today

Jen Supported Brad at Cannes in This Fringe-and-Beaded Versace Number

Honestly, It Really Doesn't Get Better Than Brad and Jen in Tuxedos

You can't argue with that statement.