Put Madonna and Tony Ward on Your ’90s Couples Style Mood Board

Madonna’s opening performance at last night’s MTV Video Music Awards had lots of surprises (Sabrina! Charli!! Debi Mazar!!! Sombr?), but for those deep in the lore, no cameo was more of a gag than Tony Ward. Madonna’s on-and-off boyfriend during the early ’90s, Ward (who made his VMAs appearance during the urinal lineup in the “Danceteria” segment) was a muse to photographer Herb Ritts and a top male model of the time. He appeared in Madonna’s Sex book and three of her music videos (most prominently in the too-hot-for-TV “Justify My Love” clip).

The pair was also spotted out and about frequently at the time, and made quite the pretty picture together. For those of you attracted to the minimal allure of Carolyn Bessette Kennedy and John F. Kennedy Jr.’s street style, but you’re looking for something a little less WASP-y and buttoned-up, might we suggest Ward and Madonna as style inspiration? While some of their projects together didn’t involve much clothing at all, when the duo was dressed up together, they were the epitome of early ’90s arty edge. They both, for example, really loved the occasional leather vest or floppy newsboy cap. To celebrate their VMAs reunion, take a trip down memory lane and revel in their singular couples style.