Rihanna Trades a 2026 Actor Awards Red Carpet Gown for a Date-Night Leather Outfit
Matching jackets with A$AP Rocky was just the start.
A$AP Rocky's If I Had Legs I'd Kick You co-star, Rose Byrne, scored a "Female Actor in a Leading Role" nomination at a 2026 Actor Awards on March 1. Even so, Rocky and Rihanna traded the red carpet for a street style serve 10 miles northwest of the Shrine Auditorium. Rihanna went one step beyond their matching leather jackets with equally glossy, over-the-knee boots.
The Laugh Factory in Hollywood doesn't honor a dress code, but that didn't stop Rihanna and A$AP Rocky from creating their own. Their one requirement? Black leather bomber jackets, a Spring 2025 trend that's staying strong a year later. RiRi led the way in the sold-out Black Ruff Rider Jacket from Willy Chavarria. It stood out on the Fall 2025 runway for its diagonal stitching, yellow gold hardware, and barrel-like sleeves. The Grammy winner made it her own with The Attico's draped mini skirt, featuring a cutout and self-tie accent atop her thigh. This allowed the elongated shafts of her thigh-high leather boots to peak through.
Her rapper boyfriend followed suit in a leather bomber, stacked on top of a black crewneck. The bottom-half of Rocky's outfit was far more casual than Rihanna's, thanks to straight-leg jeans and lived-in slim sneakers.
Rihanna and A$AP Rocky coordinated in leather bomber jackets on date night.
Leather boots this long aren't in the average knee-high collector's closet. Still, they're quintessentially Rihanna. In October 2025, she styled an almost-identical black pair from Balenciaga, featuring similar extra-pointy toe boxes. The thigh-high shafts were slightly more skintight, emerging from beneath a zip-up Acne Studios hoodie dress.
Two years ago, RiRi was spotted in L.A. wearing almost the same style.
By New Year's Eve that year, RiRi touched down in New York City with another black, over-the-knee pair by Amina Muaddi. Each extra-slouchy, leather leg matched The Attico's oversize windbreaker, plus Bottega Veneta's Kalimero Bucket Bag.
A few months later, she arrived in NYC wearing an even slouchier pair.
Judging by Rihanna's affinity for the leather shoe-turned-pants, it's a wonder she hasn't added Saint Laurent's Joe Over-the-Knee Boots to her shoe rack. (Heated Rivalry fashion guy Connor Storrie took the Fall 2025 Menswear It-Boots out after Saturday Night Live on February 28.) Boots season is still active for a few more weeks, so now's your chance, Rihanna. I'm sure Storrie would loan them to her for her next date night—she is Rihanna after all.
Shop Leather Outfits Inspired by Rihanna
