An 18-time Grand Slam champion, 35-year-old Federer keeps getting better with age. His timeless style extends to his looks on and off the court, but he really excels in classic pieces, such as blazers and slim suits. Lately, he’s been taking risks with these staples, adding in different fabrics, textures and designs, including a Gucci tuxedo with an embroidered crystal king cobra at the 2017 Met Gala.