The couple that dresses together, stays together. Well, that’s not exactly the case for all the couples on our list — some have stood the test of time while others haven’t — but all have left us with a legacy of matching couples dressing that has truly enriched our lives. From the iconic Britney Spears and Justin Timberlake denim double down to the chic fashions of Future and Ciara, we’ve got some his and hers outfits that will have you cringing, and some that will have you wanting to give your significant other’s wardrobe a makeover to match your own.
Some choose to subtly use color to match outfits, while others are not so subtle, with ties and pocket squares matching their date’s dress. Either way, celebrity couples dressing is truly a staple of the Hollywood red carpet, and with vintage favorites like J.Lo and Puff Daddy managing to pull of matching leather with gusto, we wonder why more celebrity couples don’t dabble in the art of dressing like they have one of everything for both sexes. Check out our gallery of the best matching celebrity couple’s outfits of all time, and cringe or coo along with us.
[Photo: Getty Images]