A$AP Rocky has earned the right to his self-proclaimed moniker “Fashion Killa.” For nearly a decade now, the rapper has been setting and subverting some of the biggest menswear trends. Rocky’s never been afraid to take risks, whether that means wrapping a patterned babushka around his head, wearing a sheer blouse long before sheer was even a thing, or turning a thrifted blanket into a viral Met Gala look.
Rocky’s romantic relationship with Rihanna, they now share two little ones, only helped further cement his status as music’s best-dressed man. The stylish duo understand that couples style isn’t necessarily about matching as much as it is about coordination. For Rocky, that means complimenting Rihanna’s street style with pastel Bottega Veneta suiting, double denim, and the oddball pop of color. Here, a look through A$AP Rocky’s best fashion moments.
2024: Bottega Veneta Show
Rocky had the pleasure of debuting this snakeskin Bottega Veneta bag during the brand’s spring 2025 show, before it even graced the runway or department stores. Now that’s a power move.
2024: Milan Fashion Week
Rocky leveled up something as simple as a two piece navy suit with a sculptural Bottega Veneta coat.
2024: New York Night Out
Suiting doesn’t have to be boring. Especially when achieved through color blocked mastery like the type Rocky displayed with this Bottega Veneta outfit.
2024: Bottega Veneta Show
Decked out in all leather, Rocky personified cool as he headed into Milan Fashion Week.
2023: Date Night
Rihanna’s street style is hard to match, but Rocky more than lived up to the task with a bubblegum pink Bottega Veneta bag, slouchy jeans, and pearl clips worn in his hair.
2023: Out In Los Angeles
Rocky hinted at his future Bottega Veneta ambassadorship, wearing one of the brand’s woven “Bottega Green” vests in 2023.
2023: Date Night
Joint in mouth, Bottega Veneta tote on shoulder.
2023: Met Gala
Rocky closed out the 2023 Met Gala in this custom Gucci outfit inspired by 2000s Karl Lagerfeld.
2022: Black Panther 2 Premiere
Rihanna and Rocky aren’t your average parents, so why would they opt for average fashion? The duo coordinated in olive green outfits for their first appearance after welcoming their first child, RZA.
2021: Met Gala
American brand ERL crafted Rocky’s viral 2021 Met Gala coat. The twist? It was made out of a vintage quilt from a California thrift store.
2021: New York Street Style
Rocky paired bulky ski gloves with a collared puffer coat and Adidas sneakers.
2020: Gucci Cruise Show
Rocky pulled off Alessandro Michele’s quirky Gucci separates like no other.
2020: Loewe Show
A tie-dye sweater and silver foil pants aren’t the most typical fashion pairing, but Rocky made it work during the Loewe show in 2020.
2019: Paris Fashion Week
It’s likely Rocky learned this denim styling trick—tying the hem of your jeans with a matching ribbon—from Rihanna who all but invented the look.
2019: Milan Fashion Week
Baggy denim, some quirky suiting, and a slick crossbody bag. One of Rocky’s go-to formulas.
2018: Dries Van Noten Show
Rocky’s shoe of choice to pair with this Dries Van Noten bandana moment? Black vans, naturally.
2018: LACMA Art + Film Gala
Who knew grandma’s babushka could be red carpet-appropriate? Rocky pulled out the styling trick for one of his more famous red carpet outfits during a 2018 gala.
2018: Dior Show
Before sheer was the go-to textile for female celebrities, Rocky was ahead of the curve when he wore a lace button-down to Dior’s Japan show in 2018.
2018: Calvin Klein Show
Rocky and Raf Simons for Calvin Klein? A match made in heaven.
2016: The Grammy Awards
In 2016, the rapper flouted the usual Grammy dress code in favor of this knit sweater, patchwork jeans, and Goyard bag combination.