The Swiss tennis player has a clean, classic look that barely wavers but is hardly boring: white button-downs, tailored jackets and preppy sweaters. His friendship with Vogue editrix Anna Wintour certainly helps: He frequently sits next to her at runway shows and reportedly asks her for style advice. Still Federer does have the occasional misstep, such as the ostentatious white and gold-trimmed military jacket he wore at Wimbledon in 2009.
(GIUSEPPE CACACE/AFP/Getty Images)
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