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Drake celebrated a major milestone over the weekend, bringing in his 40th birthday in New York City with several parties, celebrity guests, a performance by The Backstreet Boys and his latest footwear obsession: cowboy boots.

NEW YORK, NY - OCTOBER 24:  Drake is seen on October 24, 2026 in New York City.  (Photo by XNY/Star Max/GC Images)

Drake was spotted on Saturday in New York City. GC Images

In addition to hosting his all-black-affair pre-birthday bash the night before his birthday on Friday at Casa Cipriani, the “Pipe Down” rapper stepped out in various ensembles over the weekend. He made some strong fashion statements, including the look he was wearing when leaving an early birthday dinner at Mamo on Thursday, wrapped in a fall 1997 Hermès brown fringe shawl poncho, black leather pants and black leather shoes.

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Then on Saturday, the rapper stepped out in dark reddish-brown leather cowboy boots with a pointed-toe cap and an ornate gold-plated brass toe tip, worn with bright red leather trousers. The Grammy winner, who works with stylist Juliet Charlotte, paired the look with a cheetah-print Chrome Hearts jacket adorned with red cross accents and a white button-down shirt.

NEW YORK, NY - OCTOBER 24:  Drake is seen on October 24, 2026 in New York City.  (Photo by XNY/Star Max/GC Images)

A close-up of the shoes.

The rapper has been spotted wearing a variety of cowboy or Western-inspired boots as of late, including a pair of red Rock Revival x 424 G boots he wore to the Toronto Raptors and the Chicago Bulls at Scotiabank Arena on Oct. 21 in Toronto.

He also wore a snake-print pair of boots while out in New York. He went for a more elevated animal-inspired shoe for his all-black affair, opting for a sparkling black tuxedo jacket, black pants and the Gucci Giacomo python loafers.

NEW YORK, NY - OCTOBER 23:  Drake is seen on October 23, 2026 in New York City.  (Photo by XNY/Star Max/GC Images)

Drake is seen on Friday in New York City. GC Images

The dress shoes, which retail for $1,550, are part of Generation Gucci, which delves into the brand’s archival codes and combines different generations of design into one aesthetic narrative. The Giacomo loafer is crafted from precious leather and highlights an elongated point toe. The engraved logo detail under the sole completes the style with a discreet touch.

The shoes are made from a sleek black python leather that shimmered slightly when the lights from the camera flashes hit them. The loafers are made with a leather lining, a two-piece leather sole, a padded insole and a slight block heel.

Gucci Giacomo python loafers.

While his poncho moment went viral over the weekend, the rapper seems to be undergoing a style transformation and taking more fashion risks as he enters his fourth decade. The cowboy boots and Western-leaning shoes are a huge departure from his usual footwear. Could he perhaps be hinting at a possible genre shift in his music, the way Beyoncé Knowles-Carter did with “Cowboy Carter,” through his boots? Only time will tell.