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Drake Kicks Off His 40s in Cowboy Boots and Python Loafers for His Birthday Parties in NYC

Drake Kicks Off His 40s in Cowboy Boots and Python Loafers for His Birthday Parties in NYC

Posted on October 26, 2026

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. 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. 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. 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

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