When A$AP Rocky said "Make 'em call me Flacko Lagerfeld" in his verse for Frank Ocean's "Chanel," he had just released his highly sought-after collaboration with Guess Jeans in 2016. Little did the world know that just short of a decade later, he'd climbed not only to the top rungs of rap but also fashion, acting as Chanel's latest male ambassador.Speculation began in October when the rapper filmed a short film for Matthieu Blazy's Metiers d'Art collection in New York City. Dressed in a bold orange look and patent leather red shoes, he was a co-star of actress Margaret Qualley in the romantic short. By late November, the rapper officially announced his ambassadorship with Chanel, shortly after winning "Fashion Icon" at the 2025 CFDA Awards.For Blazy's Metiers d'Art show in December, Rocky wore a full Chanel outfit, featuring a frayed tweed jacket with a red handbag. The presentation was expectedly a women's line, yet there were a handful of looks that were styled like traditional menswear, including a Superman-inspired sweatshirt Rocky wore at Miami's Art Basel.Throughout the season, Rocky pulled out a range of other Chanel pieces at public appearances: a suede trapper hat paired with a classic quilted briefcase, new Metiers d'Art pieces, including a tweed overcoat with enlarged graphics, and more Chanel dress shoes, which he wore on Jimmy Fallon's Tonight Show.Most recently, at Blazy's Chanel Couture debut shown on Tuesday, January 27, Rocky arrived in style wearing a look anchored by a brown leather trench with monogrammed buttons and a roomy green crocodile shoulder bag. It was under Karl Lagerfeld that Chanel showed its first men’s runway looks in 2004 and continued to do so until his 2019 passing. While men’s looks can be found throughout Chanel’s collections, from RTW to Cruise, its couture-adjacent Métiers d’art line is where many men’s looks have been introduced before. The rapper is also far from the first men's ambassador, joining recent names like Kendrick Lamar, Timothee Chalamet, and Jungkook of BTS.Rocky's adoption of Chanel has fit naturally into his current, more tailored direction. While people often associate the brand's clothes with its women's tweed suiting, the rapper's appearances in the new Superman logo sweater and the leather trench coat feel more adjacent to menswear. But it's his embrace of Chanel's bags that completes these looks.Is Chanel looking to court more male customers? It's growing men's marketing strategy says so, but Blazy's first collections have continued to focus on women's, and the brand has not announced any separate men's lines. But why wait? If there's anything one can take away from Rocky's love for the brand its that men can wear womenswear, just as much as women can wear menswear.See the gallery above for a dive into A$AP Rocky's recent Chanel looks.Click here to view full gallery at Hypebeast