Rihanna and A$AP Rocky Don High-Fashion Looks at the 2025 Gotham Awards

Rihanna and A$AP Rocky had a stylish date night on the red carpet at the 2025 Gotham Awards.

Rihanna, 37, wore a drop waist gown from Balenciaga by Pierpaolo Piccioli that featured a lengthy train. She accessorized with a matching feather cap, black leather gloves and a bejeweled purple necklace.

A$AP, whose real name is Rakim Mayers, also 37, opted for a clean-cut black Chanel suit paired with black leather boots, a crisp white dress shirt, and a black and white striped tie. He completed the look with diamond-encrusted earrings.

The rapper and former Met Gala co-chair was nominated for Breakthrough Performer for his role in Spike Lee‘s Highest 2 Lowest. In a July episode of The Tonight Show Starring Jimmy Fallon, Lee, 68, said, “Yeah, don’t sleep on A$AP. In this film, Denzel [Washington] and A$AP go toe-to-toe.”

“What’s interesting is, even before I got involved with this film, I always thought that A$AP looked like he could be Denzel’s son,” the Oscar-winning director continued at the time. “There’s a big resemblance. So when you see it on the screen, it adds an element of father and son.”

Lee then revealed that he has seen other actors feel a lot of pressure when working with Washington, but that A$AP held his own.

“Don’t sleep on A$AP,” Lee began. “I’ve done five films with Denzel, and a lot of times when he’s in a scene with somebody, they just get overwhelmed. He’s one of the greatest living actors today, but A$AP wasn’t having that. Toe-to-toe, I mean, they were going at it.”

Abou Sangaré ultimately took home the win at the Gothams for Souleymane’s Story.

Ahead of the couple’s red carpet outing, Rihanna shared a glimpse at her family life, including photos from when she was pregnant with baby daughter Rocki and sons RZA, 3, and 2-year-old Riot in a Nov. 30 Instagram post as she marked Barbados Independence Day.

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“Congratulations to Barbados, MY HOME, on our 59th year of Independence and our 4th year as a Republic!” Rihanna wrote in the caption, while giving honorable mentions to Barbados’ president, Jeffrey Bostic, and Prime Minister Mia Mottley. “Barbados I L🇧🇧VE YOU!!!!” she added.

Rihanna’s post featured several photos of her and her family in her home country, including one sweet snap of RZA sitting on her lap while inspecting a piece of sugar cane and a throwback image of herself sitting with A$AP and RZA on a lawn while pregnant.