The pair dated for three years between 1994 and 1997, even getting engaged at one point, and their appearance at the 1997 premiere of The Devil's Own remains an iconic moment in their history thanks to their matching haircuts.
Now, Gwyneth has spoken about that moment, revealing that the same stylist cut their hair similarly on purpose.
WATCH: Gwyneth Paltrow shares rare Brad Pitt story
"We went to the same stylist for the cut, Chris McMillan cut both of our hair like this, " she told her assistant Kevin Keating in a video posted on Instagram
The pair were taking a look back at some of her most memorable hairstyles, as part of the release of her new GOOPGLOW Hair Serum, and the pair joked about the "matching haircuts".
"Blonde all the way to the roots in that one - and the ends," quipped Kevin, who became a fan favorite after appearing in her Netflix documentary series Goop Lab.
Brad and Gwyneth's look was cut by the same stylist
"Did you match your looks on purpose?" Kevin asked, to which Gwyneth said "no" and the pair then dissolved into giggles as Kevin joked that they should call Brad and Gwyneth exclaimed: "No, why would we call him? No one asked me about involving Brad Pitt!"
Kevin then joked that the actor was on his "Grindr" and he could "get him that way".
"OMG KEVIN NEEDS HIS OWN GOOP SERIES RIGHT NOW!!" commented TV personality Derek Blasberg,
It became an iconic look
Following her split from Brad, Gwnyeth went on to date Ben Affleck, before meeting Coldplay frontman Chris Martin in 2002.
Chris and Gwyneth wed and welcomed two children, 15-year-old son Moses and 17-year-old daughter Apple, but in 2014 shocked the world when they announced they had "consciously uncoupled".
In 2018 she married TV show producer Brad Falchuk in a star-studded private ceremony in their garden.
Gwyneth with her mom and daughter
Doting mum Gwyneth is relatively private when it comes to her family life, and it's not often that she shares photos of her loved ones. However, the star did delight fans when she posted a rare photo of her mother, fellow actress Blythe Danner.
Gwyneth uploaded a snap of herself and Blythe posing in what looked to be the living room of the star's family home in Brentwood.
In the caption, the Shallow Hal star wrote: "This beautiful creature fills our hearts with so much warmth. She gets words and names mixed up in the most hilarious and unique of ways. She is full of life and incredibly strong. She loves her grandchildren more than anything in the world. She loves Bill Evans, eating leftovers and keeping her own company.
"I admire so many things about her and today is her birthday. Happy birthday from the bottom of our hearts, your family loves you so much mommy."
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