Popsugar Fashion Celebrity Fashion Jennifer Aniston and Brad Pitt's Best Fashion Moments Brad and Jen's Most Stylish Moments Prove They Should Have Another Reunion — For Fashion's Sake 23 September 2020 by Sarah Wasilak Image Source: Backgrid 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 opinion, those instances 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 Holiday Together Image Source: Backgrid 1 / 23 Jen Redefined the Meaning of "Golden" at the 1999 Emmys Image Source: Getty / J. Vespa Hopefully Brad put his sunglasses back on. You know what they say about staring directly at the sun. 2 / 23 Jen's Elegant Red Prada Gown and Satin Shoulder Bag Stole the Show at the Emmys in 2000 Image Source: Getty / Jim Smeal Brad kept it simple, letting his lady shine — she was nominated that year for outstanding supporting actress in a comedy (Friends), after all. 3 / 23 Brad's Purple Leather Was on Another Level at the Rock Star Premiere in 2001 Image Source: Getty / Steve Granitz Jen let him revel in the spotlight this time, opting for a simple slinky tank and skirt. 4 / 23 Jen Repeated This Look in 2003, but With Boho Accessories to Flow With Brad Image Source: Getty / Jim Smeal 5 / 23 A Casual Trip to the Movies Called For Groovy Jeans Image Source: Backgrid 6 / 23 Denim and Takeout? Yeah, We've Been There Too Image Source: Backgrid 7 / 23 Jen and Brad Went For Shades of Brown at the 2002 Emmys Image Source: Getty / Gregg DeGuire Jen was glowing in vintage Christian Dior. 8 / 23 Their Leather Jackets Were Always on Point Image Source: Getty / Steve Granitz Here they are wearing their best basics in 2000 at the Erin Brockovich premiere. 9 / 23 Every Bit of This All-Black Outfit Moment Was in Sync Image Source: Getty / Peter Kramer Peep Brad's thin silver chain and Jen's silver tennis bracelet. 10 / 23 They Were California Cool With Loose Cargos and Brad's Beanie Image Source: Backgrid 11 / 23 They Packed the Most Casual Cover-Ups For Their 2005 Trip to Anguilla Image Source: Backgrid 12 / 23 When Brad Wore His Patchwork Denim, Jen Was Effortlessly Sexy in a Tank and Trousers Image Source: Getty / Steve Granitz Jen's classic look still achieves the same vibes today. 13 / 23 When Jen Took the Plunge, Brad Was There in His Best Black Tie Image Source: Getty / J. Vespa 14 / 23 Guess They Were Feeling a Neutrals Night Image Source: Getty / Jim Smeal They kept things light in his and her power suits at The Mexican premiere in 2001. 15 / 23 Nothing Is More Classic Than Jeans, Black Boots, and Fall Sweaters Image Source: Backgrid 16 / 23 Like We Said, Leather Jacket Game = Strong Image Source: Getty / Steve Granitz But get a load of Jen's furry purse! This look is classic 2000s. 17 / 23 They Certainly Knew What to Do While Accessorising in the Fall Image Source: Getty Shades clipped onto sweaters in favour of hats. 18 / 23 Jen Let Her Midriff Show and Brad Popped His Collar Image Source: Getty / Barry King They were coordinated in the subtlest of ways at the LA Fight Club premiere in 1999. 19 / 23 Jen's Vintage Chanel Dress Made Waves at the 2004 Emmys Image Source: Getty / Gregg DeGuire You can't distract from this look, right Brad? 20 / 23 Jen's Lace Slip and Strappy, Minimalist Heels Would End Up on Best Dressed Lists Today Image Source: Getty / Jim Smeal 21 / 23 Jen Supported Brad at Cannes in This Fringe-and-Beaded Versace Number Image Source: Getty / Michel Dufour 22 / 23 Honestly, It Really Doesn't Get Better Than Brad and Jen in Tuxedos Image Source: Getty / Gregg DeGuire You can't argue with that statement. 23 / 23 Celebrity FashionThe 2000sThe '90sNostalgiaCelebrity Street StyleCelebrity CouplesFall FashionJennifer AnistonRed CarpetBrad Pitt