1. Brad Pitt and Gwyneth Paltrow
Before Brad Pitt coupled up with Jennifer Aniston, he dated Gwyneth Paltrow. The pair met on the set of Se7en, and by 1996, Pitt was calling Paltrow the love of his life. Shortly after, they got engaged — but it was too good to be true. The couple broke off their engagement the following year, and we still wonder what could have been. They were known for dressing alike back in the day (peep the pic), and we'd love to see them recreate their classic outfits in 2019 (with a few modern swaps, of course). Beyond their on point style picks, their passion was undeniable.