Winnie Harlow's first public relationship was with British F1 racer, Lewis Hamilton. Their romance started to bloom in 2017, when they were pictured multiple times together at different events. They originally met in July 2017, but things started to heat up in October. They consistently tried to keep their relationship quiet to no avail (via Sun). They were last seen together in 2018, with not much known about their split (via College Candy).

Soon after Hamilton, Harlow got together with her most popular relationship yet: with Wiz Khalifa. They got together in the summer 2018, after teasing their relationship multiple times on their Instagram profiles (via College Candy). They were seen multiple times for the following months, supporting each other and looking quite adorable (via E! Online). 

Soon after their breakup in 2019, Wiz Khalifa was seen with his arms around a mystery woman and fans were quick to tag Harlow in the comments under The Shades Room's Instagram post about it. To which the model commented, per E! News, "Lol leave me out of it [red heart emoji] she's pretty tho!"