Photos: Courtesy of Brunello Cucinelli (landing page image, soccer team, candles); Courtesy of Amazon.com (book); Courtesy of Azzaro Paris (fragrance); Elissa Wiehn (pants, handkerchief); Courtesy of Moleskine (notebook); Courtesy of Trinidad (cigar); Courtesy of Everett Collection (pool); Photo by Bob Thomas / Popperfoto /Getty Images (Plato)