Zendaya and Tom Holland’s relationship has come a long way since they first met in 2016, when they were both cast in Spider-Man: Homecoming, and Zendaya was coming off a four-year relationship with her “first love.” And naturally, so has their couple style.

They might now be one of our all-time favorite couples, but Zendaya and Tom Holland started off as just a pair of coworkers with plenty of banter and have since grown before our eyes into a (reportedly) married couple. (Holland has been referring to Z as his wife during the press tour for Christopher Nolan’s The Odyssey, so it seems we are definitely past the fiancée stage, which began in 2025, when Zendaya had traded the signet she debuted in 2023 featuring Tom Holland’s initials for a stunning cushion-cut engagement ring.)

Over the years and as their relationship has grown (with matching tattoos and all), Zendaya and Holland have given us plenty of memorable looks together. They started off doing their own thing on the red carpet but have slowly but surely begun coordinating their outfits, and we are taking notes. (Lest we forget about that time they wore personalized Rangers jerseys with each other’s names and birth years!)

No matter what project she’s promoting, Zendaya is known for her showstopping looks, and whether he’s smitten by her side or supporting from afar, Holland is fully on board. The couple, even if they attend the same event, often walk red carpets solo. (But when they are promoting a project jointly like in the case of Spider-Man, which, thankfully, they frequently do, we do get to see few pics of them together.) Holland explained back in 2025 that they usually do pose solo “because it’s not my moment, it’s her moment,” adding “and if we go together, it’s about us.”

As for non-red carpet appearances, the couple keeps it casual but has over the years blessed us with a couple of joint slays, like their coordinated burgundy outfits for the launch of Holland’s non-alcoholic brand Bero, black opposing ensembles for Romeo & Juliet’s closing night at London’s West End, and even a subtle matching moment at the BNP Paribas Open.

Below, let’s revisit Zendaya and Tom Holland’s couple style evolution, from their early days as coworkers to their latest press runs and everything in between.

July 23, 2016: At Marvel Studios’ presentation during Comic-Con International